Total Synthesis of 6-Oxodendrolasinolide

Chem. J. Chinese Universities

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Total Synthesis of 6-Oxodendrolasinolide

LI Yi¹, ZHANG Tao², LI Yu-Lin¹*

1. State Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
2. Minsheng Group Shaoxing Pharmaceutical Co. Ltd., Shaoxing 312071, China

Received:2006-08-09 Revised:1900-01-01 Online:2007-07-10 Published:2007-07-10
Contact: LI Yu-Lin

Abstract

Abstract:

An efficient total synthesis of 6-oxodendrolasinolide(1), a new farnesane-type sesquiterpene lactone, was described. The synthetic route was completed from geraniol 2 and 3-methylbut-2-en-1-ol(5) through twelve steps in 5.6% overall yield. The key steps were regioselective alkylation of the anion of vinyldithian 7 with allylic chloride 4a to generate compound 8, followed by hydrolyzation of the dithiane to afford compound 9. The reduction of enone 9 gave alcohol 10, which was protected as a p-methoxylbenzylether 11. Subsequently, tetrahydropyranyl protective group was removed and oxidized to give the key intermediate aldehyde 13. Then after Corey's oxidative lactionization reaction followed by deprotection of the PMB group compound 15 was formed, which underwent Dess-Martin oxidation to afford the title compound 1.

Key words: Total synthesis, Butenolide, Sesquiterpene, Regioselectivity alkylation

CLC Number:

O621.3

TrendMD:

LI Yi¹, ZHANG Tao², LI Yu-Lin¹*. Total Synthesis of 6-Oxodendrolasinolide[J]. Chem. J. Chinese Universities, doi: .

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Total Synthesis of 6-Oxodendrolasinolide

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