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Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael\u2013Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure\u2013activity relationships within this structural type.<\/jats:p>","DOI":"10.1021\/ja506472u","type":"journal-article","created":{"date-parts":[[2014,8,15]],"date-time":"2014-08-15T14:05:02Z","timestamp":1408111502000},"page":"12137-12160","source":"Crossref","is-referenced-by-count":58,"title":["Total Synthesis\nof Viridicatumtoxin B and Analogues\nThereof: Strategy Evolution, Structural Revision, and Biological Evaluation"],"prefix":"10.1021","volume":"136","author":[{"given":"K. C.","family":"Nicolaou","sequence":"first","affiliation":[{"name":"Rice University , , 6100 Main Street , , ,","place":["Houston, Texas, United States, 77005"]},{"name":"The Scripps Research Institute , , 10550 North Torrey Pines Road , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher R. 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