Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane.
Total synthesis of the biologically important axane sesquiterpenes, gleenol (1) and axenol (2), was accomplished through a readily available spiro[4.5]decane. The key features of the synthesis of 1 and 2 include Claisen rearrangement to afford the multi-functionalized spiro[4.5]decane 4 as a single diastereomer in excellent yield, installation of the C7 isopropyl group via ketene dithioacetal instead of direct alkylation and a diastereoselective reduction of ketone under the Birch conditions.
Nakazaki
Atsuo
A
Faculty of Pharmaceutical Sciences, Tokyo University of Science, Noda, Chiba 278-8510, Japan.
Era
Tomohiro
T
Kobayashi
Susumu
S
D000470:Alkaloids / Q000138:chemical synthesis*; D000473:Alkanes / Q000737:chemistry*; D000478:Alkylation; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000473:Alkanes; D005030:Ethylenes; D007659:Ketones; D012717:Sesquiterpenes; D013141:Spiro Compounds; C526156:axenol; C526157:gleenol; C008223:ketene; C012867:decane