Issue 10, 1985

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

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1985, 637-638

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

M. Ochiai, T. Ukita, Y. Nagao and E. Fujita, J. Chem. Soc., Chem. Commun., 1985, 637 DOI: 10.1039/C39850000637

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