Trimethylene Methane Dianion Equivalent for the Asymmetric Consecutive Allylation of Aldehydes: Applications to Prins-Driven Macrocyclizations for the Synthesis of Bryostatin 1 and Analogues.
J Org Chem
; 87(23): 15925-15937, 2022 12 02.
Article
in En
| MEDLINE
| ID: mdl-36378802
ABSTRACT
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Aldehydes
/
Methane
Language:
En
Journal:
J Org Chem
Year:
2022
Document type:
Article
Affiliation country:
United States