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A concise synthesis of racemic ambrox was accomplished in a ten-step linear sequence starting from commercially available dihydroboronal with an overall yield of 20.7%. The synthetic strategy features a Br\u00f8nsted acid-mediated biomimetic cyclization of a monocyclic enol acetate and a late-stage C(sp3)\u2013H bond hydroxylation of hydrocarbons catalyzed by an activated (CO)RuII(TPFPP) complex as the key steps. Building upon this approach, an enantioselective route to (\u2212)-ambrox was successfully achieved in 11 linear steps with 14.9% overall yield by utilizing a chiral alcohol as the key intermediate, which could be conveniently prepared from the relatively inexpensive dihydro-\u03b2-ionone via Ru-catalyzed enantioselective hydrogenation of \u03b2-monocyclofarnesol.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01523","type":"journal-article","created":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T12:02:16Z","timestamp":1788955336000},"page":"12664-12673","source":"Crossref","is-referenced-by-count":0,"title":["Stereoselective\nSynthesis of (\u2212)-Ambrox via\nMetalloporphyrin-Catalyzed C(\n                    <i>sp<\/i>\n                    3)\u2013H\nBond Oxidation of Hydrocarbons"],"prefix":"10.1021","volume":"91","author":[{"given":"Cun","family":"Wang","sequence":"first","affiliation":[{"name":"Kashi University , , ,","place":["Kashgar, China, 844006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5722-7175","authenticated-orcid":true,"given":"Zhong","family":"Jin","sequence":"additional","affiliation":[{"name":"Xinjiang University , , ,","place":["Urumqi, China, 830046"]},{"name":"Xinjiang University , , ,","place":["Urumqi, China, 830046"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,9]]},"reference":[{"key":"2026091808081728300_cit1","doi-asserted-by":"publisher","first-page":"5042","DOI":"10.1021\/acs.jafc.2c09010","article-title":"From ambergris to (\u2212)-ambrox: Chemistry meets\nbiocatalysis for sustainable (\u2212)-ambrox production","volume":"71","author":"Eichhorn","year":"2023","journal-title":"J. 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