Synthesis of (±)-lecanindole D

Akiko Asanuma; Masaru Enomoto; Tomohiro Nagasawa; Shigefumi Kuwahara

doi:10.1016/j.tetlet.2013.06.084

Synthesis of (±)-lecanindole D

Akiko Asanuma, Masaru Enomoto, Tomohiro Nagasawa, Shigefumi Kuwahara

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

19 Citations (Scopus)

Abstract

The first synthesis of the racemate of lecanindole D, an indole sesquiterpenoid with potent and selective agonist activity toward the progesterone receptor, has been achieved from a known tetracyclic alcohol by using a diastereoselective installation of its tertiary hydroxy group via an epoxide intermediate and a Pd(II)-mediated construction of the indole ring moiety as the key transformations.

Original language	English
Pages (from-to)	4561-4563
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2013.06.084
Publication status	Published - 2013 Aug 21

Keywords

Alkaloid
Indole sesquiterpene
Lecanindole
Progesterone receptor agonist

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.06.084

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title = "Synthesis of (±)-lecanindole D",

abstract = "The first synthesis of the racemate of lecanindole D, an indole sesquiterpenoid with potent and selective agonist activity toward the progesterone receptor, has been achieved from a known tetracyclic alcohol by using a diastereoselective installation of its tertiary hydroxy group via an epoxide intermediate and a Pd(II)-mediated construction of the indole ring moiety as the key transformations.",

keywords = "Alkaloid, Indole sesquiterpene, Lecanindole, Progesterone receptor agonist",

author = "Akiko Asanuma and Masaru Enomoto and Tomohiro Nagasawa and Shigefumi Kuwahara",

note = "Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 23780112 ). ",

year = "2013",

month = aug,

day = "21",

doi = "10.1016/j.tetlet.2013.06.084",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Synthesis of (±)-lecanindole D

AU - Asanuma, Akiko

AU - Enomoto, Masaru

AU - Nagasawa, Tomohiro

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 23780112 ).

PY - 2013/8/21

Y1 - 2013/8/21

N2 - The first synthesis of the racemate of lecanindole D, an indole sesquiterpenoid with potent and selective agonist activity toward the progesterone receptor, has been achieved from a known tetracyclic alcohol by using a diastereoselective installation of its tertiary hydroxy group via an epoxide intermediate and a Pd(II)-mediated construction of the indole ring moiety as the key transformations.

AB - The first synthesis of the racemate of lecanindole D, an indole sesquiterpenoid with potent and selective agonist activity toward the progesterone receptor, has been achieved from a known tetracyclic alcohol by using a diastereoselective installation of its tertiary hydroxy group via an epoxide intermediate and a Pd(II)-mediated construction of the indole ring moiety as the key transformations.

KW - Alkaloid

KW - Indole sesquiterpene

KW - Lecanindole

KW - Progesterone receptor agonist

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Synthesis of (±)-lecanindole D

Abstract

Keywords

ASJC Scopus subject areas

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