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Total syntheses of naturally occurring diacetylenic spiroacetal enol ethers.

The Journal of organic chemistry (2005-07-16)
Naoki Miyakoshi, Daisuke Aburano, Chisato Mukai
ABSTRACT

A highly stereoselective method for constructing a (2E)-methoxymethylidene-1,6-dioxaspiro[4.5]decane skeleton has been developed on the basis of the palladium(II)-catalyzed ring-closing reaction of the 3,4-dioxygenated-9-hydroxy-1-nonyn-5-one derivatives as a crucial step. The newly developed procedures could be successfully applied to the first total synthesis of five diacetylenic spiroacetal enol ether natural products starting from commercially available (R,R)- or (S,S)-diethyl tartrate.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diethyl L-tartrate, ≥99%, FG
Sigma-Aldrich
(+)-Diethyl L-tartrate, ≥99%
Sigma-Aldrich
(−)-Diethyl D-tartrate, ≥99%