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Synthesis and photolysis of some carbohydrate 1,6-dienes

✍ Scribed by Robert J. Ferrier; Peter C. Tyler

Book ID
102991057
Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
793 KB
Volume
136
Category
Article
ISSN
0008-6215

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✦ Synopsis

Several attempts to abbreviate our earlier syntheses of the prostaglandin intermediates 4 and 5 by photocyclisation of carbohydrate-based 1,6-dienes (15-18, 20, 22) did not yield the required bicyclo[3.2.0]heptane derivatives. Photolysis of 7-O-tert-butyldimethylsilyl-1,3,4,5,8,9-hexadeoxy-6-O-methoxymethyl-~-threonon-3,8-dien-2-ulose (20) and ethyl 6-0-tert-butyldimethylsilyl-2,3,4,7,8-pentadeoxy-5-O-methoxymethyl-D-threo-oct-2,7-dienonate ( 22) caused migration of the conjugated alkene bond.

πŸ“œ SIMILAR VOLUMES

Metathesis reactions of Ξ²-acyloxysulfone
Metathesis reactions of Ξ²-acyloxysulfones: synthesis of 1,6- and 1,7-dienes
✍ Gregory W. O’Neil; Daniel J. Moser; Erasmus O. Volz πŸ“‚ Article πŸ“… 2009 πŸ› Elsevier Science 🌐 French βš– 349 KB

A novel alkene-masking strategy has been developed that allows for a metathesis approach to 1,6-and 1,7-dienes. This method was successfully applied to the synthesis of a long-chain alkenone natural product.