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Total synthesis of dextro 9 10 syn and dextro 9 10 anti copalol via epoxy trienylsilane cyclizations



Total synthesis of dextro 9 10 syn and dextro 9 10 anti copalol via epoxy trienylsilane cyclizations



Journal of Organic Chemistry 57(17): 4598-4608



Total syntheses of (+)-9,10-syn-copalol, the pyrophosphate ester of which is a likely intermediate in the biosynthesis of 9,10-syn diterpenes, and its 9,10-anti isomer are reported. Lithiation of (-)-(6R)-6,7-epoxygeranyl p-tolylsulfone (-) or (.+-.) followed by alkylation with (E,Z)- and (E,E)-8-bromo-9-(trimethylsilyl)geranyl benzyl ethers and selective reductive cleavage of the toluenesulfonyl and benzyl groups afforded (2E,6E,10E,14R)- and (2E,6Z,10E,14R)-14,15-epoxy-19-(trimethylsilyl)geranylgeraniols ((-)- and (.+-.). Lewis acid treatment of the benzoate and/or acetates of (-)-24a and (.+-.)-26a effected efficient but almost stereorandom bicyclizations to 9,10-syn- and 9,10-anti-labda-8(17),13(E)-diene-3.beta.,15-diol esters which were converted to (+)-9,10-syn- and (+)-9,10-anti-copalol.

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