Tandem intramolecular silylformylation-crotylsilylation: highly efficient synthesis of polyketide fragments.
Polyketide fragments may be rapidly and efficiently assembled in the tandem intramolecular silylformylation-crotylsilylation of alkenes and alkynes. The reactions establish up to three new stereocenters with good-to-excellent diastereoselectivity, and the use of the reaction in an iterative sense is demonstrated. In addition, a new dihydrosilane alcoholysis reaction has been developed, leading to a highly efficient sequence.
Zacuto
Michael J
MJ
Department of Chemistry, Columbia University, New York, New York 10027, USA.
O'Malley
Steven J
SJ
Leighton
James L
JL
D000438:Alcohols / Q000138:chemical synthesis*; D011108:Polymers / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*
D000438:Alcohols; D011108:Polymers; D012821:Silanes; C024617:polyol