Synthesis of diazatricyclic common structure of madangamine alkaloids

Yuta Yanagita; Takahiro Suto; Naoya Matsuo; Yasuhiro Kurosu; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.5b00661

Synthesis of diazatricyclic common structure of madangamine alkaloids

Yuta Yanagita, Takahiro Suto, Naoya Matsuo, Yasuhiro Kurosu, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

20 Citations (Scopus)

Abstract

A general synthetic route toward a diazatricyclic core common to the madangamine family is described. Ring-closing metathesis and palladium-catalyzed cycloisomerization provided the cis-fused diazadecalin structure, accompanied by formation of the N-Boc-enamine, which was utilized as an N-acyliminium ion equivalent. Direct cyclization from the N-Boc-enamine was achieved through the in situ formation of an N,O-acetal.

Original language	English
Pages (from-to)	1946-1949
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.5b00661
Publication status	Published - 2015 Apr 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5b00661

Cite this

@article{8ea49a5c0a414efa835a1e39f1cca3fe,

title = "Synthesis of diazatricyclic common structure of madangamine alkaloids",

abstract = "A general synthetic route toward a diazatricyclic core common to the madangamine family is described. Ring-closing metathesis and palladium-catalyzed cycloisomerization provided the cis-fused diazadecalin structure, accompanied by formation of the N-Boc-enamine, which was utilized as an N-acyliminium ion equivalent. Direct cyclization from the N-Boc-enamine was achieved through the in situ formation of an N,O-acetal.",

author = "Yuta Yanagita and Takahiro Suto and Naoya Matsuo and Yasuhiro Kurosu and Takaaki Sato and Noritaka Chida",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = apr,

day = "17",

doi = "10.1021/acs.orglett.5b00661",

language = "English",

volume = "17",

pages = "1946--1949",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Synthesis of diazatricyclic common structure of madangamine alkaloids

AU - Yanagita, Yuta

AU - Suto, Takahiro

AU - Matsuo, Naoya

AU - Kurosu, Yasuhiro

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2015/4/17

Y1 - 2015/4/17

N2 - A general synthetic route toward a diazatricyclic core common to the madangamine family is described. Ring-closing metathesis and palladium-catalyzed cycloisomerization provided the cis-fused diazadecalin structure, accompanied by formation of the N-Boc-enamine, which was utilized as an N-acyliminium ion equivalent. Direct cyclization from the N-Boc-enamine was achieved through the in situ formation of an N,O-acetal.

AB - A general synthetic route toward a diazatricyclic core common to the madangamine family is described. Ring-closing metathesis and palladium-catalyzed cycloisomerization provided the cis-fused diazadecalin structure, accompanied by formation of the N-Boc-enamine, which was utilized as an N-acyliminium ion equivalent. Direct cyclization from the N-Boc-enamine was achieved through the in situ formation of an N,O-acetal.

UR - http://www.scopus.com/inward/record.url?scp=84928037110&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84928037110&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b00661

DO - 10.1021/acs.orglett.5b00661

M3 - Article

C2 - 25815528

AN - SCOPUS:84928037110

SN - 1523-7060

VL - 17

SP - 1946

EP - 1949

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Synthesis of diazatricyclic common structure of madangamine alkaloids

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this