Trimethylene Methane Dianion Equivalent for the Asymmetric Consecutive Allylation of Aldehydes: Applications to Prins-Driven Macrocyclizations for the Synthesis of Bryostatin 1 and Analogues.

Autor:	Wender PA; Department of Chemistry, Stanford University, Stanford, California 94305, United States.; Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305, United States., Luu-Nguyen QH; Department of Chemistry, Stanford University, Stanford, California 94305, United States., Sloane JL; Department of Chemistry, Stanford University, Stanford, California 94305, United States., Ranjan A; Department of Chemistry, Stanford University, Stanford, California 94305, United States.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2022 Dec 02; Vol. 87 (23), pp. 15925-15937. Date of Electronic Publication: 2022 Nov 15.
DOI:	10.1021/acs.joc.2c02047
Abstrakt:	We report a one-step (one-flask) generation and reaction of a bifunctional allylating reagent, a trimethylene methane dianion equivalent, that provides a route for the asymmetric 2-(trimethylsilylmethyl) allylation of aldehydes. The product of the first aldehyde allylation process is then set to engage in a second separate aldehyde allylation, providing an improved Prins macrocyclization strategy both for the scalable synthesis of bryostatin 1 and for the total synthesis of a new potent bryostatin analogue.
Databáze:	MEDLINE
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