Issue 30, 2021

Bismuth(iii)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones

Abstract

Herein we disclose an unprecedented intramolecular cascade strategy for the construction of α,β-unsaturated [5,5]- and [6,5]-oxaspirolactones that capitalizes on the π-electrophilic Lewis acid-catalyzed 5-exo-dig or 6-exo-dig mode of cyclization of propargylic diol esters, followed by dehydration and spirolactonization steps. Moreover, semi-protected substrates also delivered the respective oxaspirolactones with the same ease and in appreciable yields under optimal reaction conditions.

Graphical abstract: Bismuth(iii)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones

Supplementary files

Article information

Article type
Communication
Submitted
20 May 2021
Accepted
07 Jul 2021
First published
07 Jul 2021

Org. Biomol. Chem., 2021,19, 6618-6622

Bismuth(III)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones

D. A. Kambale, B. R. Borade and R. Kontham, Org. Biomol. Chem., 2021, 19, 6618 DOI: 10.1039/D1OB00974E

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