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

TitleBismuth(iii)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones
Publication TypeJournal Article
Year of Publication2021
AuthorsKambale, DA, Borade, BR, Kontham, R
JournalOrganic & Biomolecular Chemistry
Volume19
Issue30
Pagination6618-6622
Date PublishedAUG
Type of ArticleArticle
ISSN1477-0520
AbstractHerein we disclose an unprecedented intramolecular cascade strategy for the construction of alpha,beta-unsaturated [5,5]- and [6,5]-oxaspirolactones that capitalizes on the pi-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.
DOI10.1039/d1ob00974e
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.876
Divison category: 
Organic Chemistry