[4+1] Cyclizations to Enantiopure Multifunctional Cyclopentanes from d -Glucose Using Formyl Dianion Synthons

authored by

Andreas Kirschning, Ernst Schaumann, Nico Bräuer, Tycho Michel, Silke Oelze

Abstract

The [4+1] cyclization of a sugar-based epoxytosylate with various C1 dianion equivalents provide highly functionalized homochiral cyclopentane derivatives. For these, a follow-up chemistry was developed to provide various cyclopentane building blocks as starting points for natural product syntheses. The [4+1] domino protocol relies on a 1,4-Brook rearrangement, which is essential for generating the second carbanion.

Organisation(s)

Institute of Organic Chemistry

External Organisation(s)

Clausthal University of Technology

Type

Article

Journal

SYNLETT

Volume

35

Pages

973-978

No. of pages

6

ISSN

0936-5214

Publication date

2024

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Organic Chemistry

Electronic version(s)

https://doi.org/10.1055/a-2201-3861 (Access: Closed)