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Stereoselective synthesis of cembranolide precursors via macrocyclization of α-alkoxyallylstannane aldehydes

✍ Scribed by James A. Marshall; Bradley S. DeHoff; Stephen L. Crooks

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
293 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 -78°C.

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