Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Reviews and Accounts
Synthesis of Polyacetate and Acetate-propionate Hybrid-type Polyketides Using Novel Remote Asymmetric Induction Reactions
Seijiro Hosokawa
Author information
JOURNAL RESTRICTED ACCESS

2021 Volume 79 Issue 2 Pages 109-119

Details
Abstract

Polyacetate-type and acetate-propionate hybrid-type polyketide skeletons have been constructed by the remote asymmetric induction of the vinylogous Mukaiyama aldol reactions using chiral oxazolidinone-attached vinylketene silyl N,O-acetals. In the acetate-propionate hybrid-type reaction, anti- and syn-adducts were selectively afforded using aldehydes and acetals, respectively. Therefore, in conjunction with the previously reported polypropionate-type reaction, all types of polyketide skeletons have been able to be synthesized. In addition to the transition states of the acetate-propionate hybrid-type reactions, difference of the stereo-control systems between the polyacetate-type reaction and the polypropionate-type reaction is discussed. Interestingly, in polyacetate-type and acetate-propionate hybrid-type reactions, the chiral auxiliary controlled the stereoselectivity indirectly. Additionally, (S)-massoialactone (α,β-unsaturated δ-lactone) and tabtoxinine-β-lactam, an inhibitor of glutamate synthetase, were synthesized by the remote asymmetric induction reactions.

Content from these authors
© 2021 The Society of Synthetic Organic Chemistry, Japan
Previous article Next article
feedback
Top