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

58 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

Access to Document

10.1021/ol500903e

Fingerprint Dive into the research topics of 'Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis'. Together they form a unique fingerprint.

Cite this

@article{7336b01f35d0412bbaecae95a6565f9b,

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

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",

year = "2014",

month = may,

day = "2",

doi = "10.1021/ol500903e",

language = "English",

volume = "16",

pages = "2526--2529",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

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.

UR - http://www.scopus.com/inward/record.url?scp=84899820295&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84899820295&partnerID=8YFLogxK

U2 - 10.1021/ol500903e

DO - 10.1021/ol500903e

M3 - Article

C2 - 24754345

AN - SCOPUS:84899820295

VL - 16

SP - 2526

EP - 2529

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -