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Stereoselective synthesis of cembranolides via conjugate addition to cycloalkynones

โœ Scribed by James A. Marshall; Stephen L. Crooks

Book ID
108382794
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
160 KB
Volume
28
Category
Article
ISSN
0040-4039

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๐Ÿ“œ SIMILAR VOLUMES

Stereoselective synthesis of cembranolid
Stereoselective synthesis of cembranolide precursors via macrocyclization of ฮฑ-alkoxyallylstannane aldehydes
โœ James A. Marshall; Bradley S. DeHoff; Stephen L. Crooks ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 293 KB

An efficient route to the MOM-protected a-hydroxylallylstannane propargylic aldehyde 15 starting from geraniolis described. Cyclization of 15 to the 1Cmembered cembranolide intermediate 16, a 7:l mixture of cis and trans isomers, is effected in 80% yield with BF3. OEtz at -78ยฐC.