{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T05:19:19Z","timestamp":1788326359187,"version":"build-2803163510"},"reference-count":65,"publisher":"American Chemical Society (ACS)","issue":"34","license":[{"start":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T00:00:00Z","timestamp":1786492800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T00:00:00Z","timestamp":1786492800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T00:00:00Z","timestamp":1786492800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["DP200101448"],"award-info":[{"award-number":["DP200101448"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["DP210103053"],"award-info":[{"award-number":["DP210103053"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["FT200100049"],"award-info":[{"award-number":["FT200100049"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Monash Warwick Alliance Initiative in Combatting Emerging Superbug Threats","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The bisabosquals are a family of natural products from Stachybotrys fungi with mixed polyketide terpene biosynthetic origin. These meroterpenoids feature complex and unique substructures, displaying a benzofuran-fused benzopyran, with 5-contiguous stereocenters, and all-cis ring fusion about the bisabolane-cyclohexyl ring. Additionally, the pentasubstituted aromatic ring features diverse substitution patterns that influence the bioactivity of the specific bisabosqual, which include antifungal, antiproliferative and mammalian squalene synthase inhibition. Interest in their chemical synthesis has largely focused on the tetracyclic core structure with the diverse arene substitutions unaddressed. Herein, we report studies investigating the viability of late-stage aromatic ring functionalization strategies designed to provide divergent access to bisabosqual natural products bearing differential functionality in the aromatic ring. While these studies ultimately proved unsuccessful, insights from these investigations informed our recently reported enantioselective total synthesis of (\u2212)-bisabosqual F. Full details of these studies and extension of this work to the first enantioselective total synthesis of (+)-bisabosqual A are communicated herein.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01205","type":"journal-article","created":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T17:01:48Z","timestamp":1786554108000},"page":"11732-11741","source":"Crossref","is-referenced-by-count":0,"title":["Enantioselective\nTotal Synthesis of (+)-Bisabosqual\nA and Studies on Late-Stage C(sp3)\u2013H Functionalization\nApproaches to Bisabosquals"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-2821-2172","authenticated-orcid":true,"given":"James P.","family":"Shephard","sequence":"first","affiliation":[{"name":"Monash University , , , ,","place":["Clayton, Victoria, Australia, 3800"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adam","family":"Ametovski","sequence":"additional","affiliation":[{"name":"Monash University , , , ,","place":["Clayton, Victoria, Australia, 3800"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6859-172X","authenticated-orcid":true,"given":"Alasdair I.","family":"McKay","sequence":"additional","affiliation":[{"name":"Monash University , , , ,","place":["Clayton, Victoria, Australia, 3800"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3249-0828","authenticated-orcid":true,"given":"Lauren A. M.","family":"Murray","sequence":"additional","affiliation":[{"name":"Monash University , , , ,","place":["Clayton, Victoria, Australia, 3800"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5515-2878","authenticated-orcid":true,"given":"Alex C.","family":"Bissember","sequence":"additional","affiliation":[{"name":"University of Tasmania , , ,","place":["Hobart, Australia, 7001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0958-4298","authenticated-orcid":true,"given":"David W.","family":"Lupton","sequence":"additional","affiliation":[{"name":"Monash University , , , ,","place":["Clayton, Victoria, Australia, 3800"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,12]]},"reference":[{"key":"2026090200062737100_cit1a","doi-asserted-by":"publisher","first-page":"890","DOI":"10.7164\/antibiotics.54.890","article-title":"Bisabosquals, novel squalene synthase\ninhibitors. I. Taxonomy, fermentation, isolation and biological activities","volume":"54","author":"Minagawa","year":"2001","journal-title":"J. Antibiot."},{"key":"2026090200062737100_cit1b","doi-asserted-by":"publisher","first-page":"896","DOI":"10.7164\/antibiotics.54.896","article-title":"Bisabosquals,\nNovel Squalene Synthase Inhibitors. II. Physico-chemical Properties\nand Structure Elucidation","volume":"54","author":"Minagawa","year":"2001","journal-title":"J. Antibiot."},{"key":"2026090200062737100_cit2a","doi-asserted-by":"publisher","first-page":"1644","DOI":"10.1039\/D0OB02162H","article-title":"The chemistry\nand biology of fungal meroterpenoids (2009\u20132019)","volume":"19","author":"Jiang","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"2026090200062737100_cit2b","doi-asserted-by":"publisher","first-page":"623","DOI":"10.1007\/s11101-014-9365-1","article-title":"Chemical and\nbioactive diversities of the genera Stachybotrys and Memnoniella secondary\nmetabolites","volume":"14","author":"Wang","year":"2015","journal-title":"Phytochem. Rev."},{"key":"2026090200062737100_cit2c","doi-asserted-by":"publisher","first-page":"1063","DOI":"10.1039\/b820413f","article-title":"Meroterpenoids produced by fungi","volume":"26","author":"Geris","year":"2009","journal-title":"Nat. Prod. Rep."},{"key":"2026090200062737100_cit3a","doi-asserted-by":"publisher","first-page":"803","DOI":"10.1039\/D5NP00085H","article-title":"Isolation and synthesis\nof bisabosquals, fungal triprenyl phenol meroterpenoids with a densely\nfunctionalised bisabolane core","volume":"43","author":"Shephard","year":"2026","journal-title":"Nat. Prod. Rep."},{"key":"2026090200062737100_cit3b","doi-asserted-by":"publisher","first-page":"666","DOI":"10.1039\/c8np00072g","article-title":"Synthetic approaches\nto natural products containing 2,3-dihydrobenzofuran skeleton","volume":"36","author":"Chen","year":"2019","journal-title":"Nat. Prod. Rep."},{"key":"2026090200062737100_cit4","doi-asserted-by":"publisher","first-page":"1577","DOI":"10.3390\/molecules23071577","article-title":"New bisabosquals\nfrom stachybotrys sp. 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Ed."},{"key":"2026090200062737100_cit15d","doi-asserted-by":"publisher","first-page":"415","DOI":"10.1055\/s-0036-1588109","article-title":"All-carbon (4 +\n2) annulations catalysed by N-heterocyclic carbenes","volume":"28","author":"Levens","year":"2017","journal-title":"Synlett"},{"key":"2026090200062737100_cit16a","doi-asserted-by":"publisher","first-page":"1212","DOI":"10.1021\/acs.orglett.9b00198","article-title":"Enantioselective\nTotal Synthesis of (\u2212)-\u03949-Tetrahydrocannabinol\nvia N-Heterocyclic Carbene Catalysis","volume":"21","author":"Ametovski","year":"2019","journal-title":"Org. Lett."},{"key":"2026090200062737100_cit16b","doi-asserted-by":"publisher","first-page":"11686","DOI":"10.1002\/anie.201203704","article-title":"Continuum of Progress: Applications of N-Hetereocyclic\nCarbene Catalysis in Total Synthesis","volume":"51","author":"Izquierdo","year":"2012","journal-title":"Angew.\nChem., Int. 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Soc."},{"key":"2026090200062737100_cit17e","doi-asserted-by":"publisher","first-page":"195","DOI":"10.1038\/nature12472","article-title":"Stereoinversion\nof tertiary alcohols to tertiary-alkyl isonitriles and amines","volume":"501","author":"Pronin","year":"2013","journal-title":"Nature"},{"key":"2026090200062737100_cit17f","doi-asserted-by":"publisher","first-page":"9378","DOI":"10.1039\/D0SC02562C","article-title":"Stereospecific nucleophilic substitution at tertiary and quaternary\nstereocentres","volume":"11","author":"Lanke","year":"2020","journal-title":"Chem. Sci."},{"key":"2026090200062737100_cit17g","doi-asserted-by":"publisher","first-page":"1451","DOI":"10.1016\/j.chempr.2020.11.022","article-title":"Stereospecific and stereoconvergent\nnucleophilic substitution reactions at tertiary carbon centers","volume":"7","author":"Zhang","year":"2021","journal-title":"Chem"},{"key":"2026090200062737100_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202524461","article-title":"Enantioselective Total Synthesis\nof (\u2212)-Bisabosqual F via N-Heterocyclic Carbene Catalyzed (4\n+ 2) Annulation","volume":"65","author":"Shephard","year":"2026","journal-title":"Angew. Chem., Int. 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Commun."},{"key":"2026090200062737100_cit22b","doi-asserted-by":"publisher","first-page":"2713","DOI":"10.1055\/s-0034-1380429","article-title":"Total Synthesis\nof Rhododaurichromanic Acid A","volume":"47","author":"Luo","year":"2015","journal-title":"Synthesis"},{"key":"2026090200062737100_cit22c","doi-asserted-by":"publisher","first-page":"1250","DOI":"10.1039\/c3ob42110d","article-title":"One-Pot Synthesis of Cannabicyclol and Related Polycycles","volume":"12","author":"Li","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"2026090200062737100_cit23a","doi-asserted-by":"publisher","first-page":"12479","DOI":"10.1039\/D0CC04863A","article-title":"Traceless Directing Groups in C\u2013H Functionalization","volume":"56","author":"Rani","year":"2020","journal-title":"Chem. 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Chem."},{"key":"2026090200062737100_cit24a","doi-asserted-by":"publisher","first-page":"252","DOI":"10.1126\/science.aad7893","article-title":"Functionalization of C(sp3)\u2013H Bonds Using Transient\nDirecting Groups","volume":"351","author":"Zhang","year":"2016","journal-title":"Science"},{"key":"2026090200062737100_cit24b","doi-asserted-by":"publisher","first-page":"12192","DOI":"10.1039\/D0RA01927E","article-title":"Pd-Catalyzed C(sp3)\u2013H Acetoxylation\nof Aldehydes","volume":"10","author":"Chen","year":"2020","journal-title":"RSC Adv."},{"key":"2026090200062737100_cit25","doi-asserted-by":"publisher","first-page":"112","DOI":"10.1039\/jr9590000112","article-title":"Stereoselective Synthesis of Olefins","author":"Cornforth","year":"1959","journal-title":"J. Chem. 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