Stereochemistry of an oxidative 1,4-fragmentation of γ-stannyl alcohols with a hypervalent organoiodine compound and the synthesis of erythro-6-acetoxyhexadecan-5-olide
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 10,p. 637-638
- https://doi.org/10.1039/c39850000637
Abstract
Iodine(III)-mediated oxidative 1,4-fragmentation of the 2,3-trans- and 2,3-cis-3-stannyl alcohols, (6a,b) and (6c), proceeds stereospecifically to give the E- and Z-enals, (7) and (8), respectively, and stetreoselective synthesis of the mosquito pheromone, erythro-6-acetoxyhexadecan-5-olide (5), starting from the E-enal(7), was accomplished.Keywords
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