Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

Atsushi Umehara; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1021/ol500903e

Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

Atsushi Umehara, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

Original language	English
Pages (from-to)	2526-2529
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	9
DOIs	https://doi.org/10.1021/ol500903e
Publication status	Published - 2014 May 2

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol500903e

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abstract = "Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.",

author = "Atsushi Umehara and Hirofumi Ueda and Hidetoshi Tokuyama",

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AU - Umehara, Atsushi

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

PY - 2014/5/2

Y1 - 2014/5/2

N2 - Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

AB - Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

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Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

Abstract

ASJC Scopus subject areas

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