Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols

Davis, Dexter C.; Walker, Katherine L.; Hu, Chunhua; Zare, Richard N.; Waymouth, Robert M.; Dai, Mingji

doi:10.1021/jacs.6b06573

Title: Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols

Journal Article · Tue Jul 26 00:00:00 EDT 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b06573· OSTI ID:1467609

Davis, Dexter C. ^[1]; Walker, Katherine L. ^[2]; Hu, Chunhua ^[3]; Zare, Richard N. ^[2]; Waymouth, Robert M. ^[2]; Dai, Mingji ^[1]

Purdue Univ., West Lafayette, IN (United States)
Stanford Univ., Stanford, CA (United States)
New York Univ. (NYU), NY (United States)

A palladium-catalyzed cascade carbonylative spirolactonization of hydroxycyclopropanols has been developed to efficiently synthesize oxaspirolactones common to many complex natural products of important therapeutic value. The mild reaction conditions, high atom economy, broad substrate scope, and scalability of this new method were highlighted in expedient total syntheses of the Turkish tobacco natural products α-levantanolide and α-levantenolide in two and four steps respectively. The hydroxycyclopropanol substrates are readily available in one step via a Kulinkovich reaction of the corresponding lactones. Mechanistic studies utilizing high-resolution electrospray ionization mass spectrometry (ESI-MS) identified several key intermediates in the catalytic cycle as well as those related to catalyst decomposition and competitive pathways.

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Research Organization:: Stanford Univ., CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0005430

OSTI ID:: 1467609

Journal Information:: Journal of the American Chemical Society, Vol. 138, Issue 33; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 89 works

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