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Total syntheses and stereochemical reassignments of mollenines A and B.

Abstract：

:Total syntheses of prenylated pyrrolidinoindoline alkaloids, (-)-mollenines A [(-)-1'] and B (2'), were accomplished via three- and four-step sequences including a bioinspired indole prenylation reaction followed by dioxomorpholine ring formation. Then, the stereochemistry of mollenines A and B was reassigned to 3S,6S,14S,16S by analysis of spectroscopic data and chemical syntheses with different approaches along with the comparison of calculated and experimental ECD spectra. In addition, a thermodynamically controlled epimerization reaction on the dioxomorpholine ring was observed in our synthesis.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Shiomi S,Wada K,Umeda Y,Kato H,Tsukamoto S,Ishikawa H

doi

10.1016/j.bmcl.2018.01.065

subject

Has Abstract

pub_date

2018-09-01 00:00:00

pages

2766-2769

issue

16

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(18)30076-3

journal_volume

28

pub_type

杂志文章

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