Total synthesis of methyl sarcophytoate, a marine natural biscembranoid

Takahiro Ichige, Yusuke Okano, Naoki Kanoh, Masaya Nakata

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

(Chemical Equation Presented) The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu2Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu2Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, π-face, and regioselectivities. During this reaction, partial E → Z isomerization at the C4 position was observed.

Original languageEnglish
Pages (from-to)230-243
Number of pages14
JournalJournal of Organic Chemistry
Volume74
Issue number1
DOIs
Publication statusPublished - 2009 Jan 2

Fingerprint

Regioselectivity
Epoxidation
Cyclization
Epoxy Compounds
Isomerization
methyl sarcophytoate
n-butyllithium
Hot Temperature
dithiane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of methyl sarcophytoate, a marine natural biscembranoid. / Ichige, Takahiro; Okano, Yusuke; Kanoh, Naoki; Nakata, Masaya.

In: Journal of Organic Chemistry, Vol. 74, No. 1, 02.01.2009, p. 230-243.

Research output: Contribution to journalArticle

Ichige, Takahiro ; Okano, Yusuke ; Kanoh, Naoki ; Nakata, Masaya. / Total synthesis of methyl sarcophytoate, a marine natural biscembranoid. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 1. pp. 230-243.
@article{ef279f3b675b45618ab70d1a661a5c3f,
title = "Total synthesis of methyl sarcophytoate, a marine natural biscembranoid",
abstract = "(Chemical Equation Presented) The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu2Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu2Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, π-face, and regioselectivities. During this reaction, partial E → Z isomerization at the C4 position was observed.",
author = "Takahiro Ichige and Yusuke Okano and Naoki Kanoh and Masaya Nakata",
year = "2009",
month = "1",
day = "2",
doi = "10.1021/jo802249k",
language = "English",
volume = "74",
pages = "230--243",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Total synthesis of methyl sarcophytoate, a marine natural biscembranoid

AU - Ichige, Takahiro

AU - Okano, Yusuke

AU - Kanoh, Naoki

AU - Nakata, Masaya

PY - 2009/1/2

Y1 - 2009/1/2

N2 - (Chemical Equation Presented) The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu2Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu2Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, π-face, and regioselectivities. During this reaction, partial E → Z isomerization at the C4 position was observed.

AB - (Chemical Equation Presented) The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu2Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu2Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, π-face, and regioselectivities. During this reaction, partial E → Z isomerization at the C4 position was observed.

UR - http://www.scopus.com/inward/record.url?scp=58149316212&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=58149316212&partnerID=8YFLogxK

U2 - 10.1021/jo802249k

DO - 10.1021/jo802249k

M3 - Article

C2 - 19053598

AN - SCOPUS:58149316212

VL - 74

SP - 230

EP - 243

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 1

ER -