Grubbs carbene complex-catalyzed cleavage of allyl vic-diols to aldehydes with a co-oxidant

Application to the selective cleavage of huge marine molecules

Chunguang Han, Yoshi Yamano, Fumitoshi Kakiuchi, Kazuhiko Nakamura, Daisuke Uemura

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An oxidative cleavage of allyl vic-diols to aldehydes catalyzed by a Grubbs carbene complex using a co-oxidant has been established for the first time, with good yields. The utility of this selective cleavage reaction was demonstrated through the use of two huge marine molecules, symbiodinolide and N-p-BrBz palytoxin.

Original languageEnglish
Pages (from-to)9622-9626
Number of pages5
JournalTetrahedron
Volume67
Issue number49
DOIs
Publication statusPublished - 2011 Dec 9

Fingerprint

Oxidants
Aldehydes
Molecules
palytoxin
symbiodinolide
carbene

Keywords

  • Catalytic reaction
  • Degradation reaction
  • Grubbs carbene complex
  • Marine huge molecule

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Grubbs carbene complex-catalyzed cleavage of allyl vic-diols to aldehydes with a co-oxidant : Application to the selective cleavage of huge marine molecules. / Han, Chunguang; Yamano, Yoshi; Kakiuchi, Fumitoshi; Nakamura, Kazuhiko; Uemura, Daisuke.

In: Tetrahedron, Vol. 67, No. 49, 09.12.2011, p. 9622-9626.

Research output: Contribution to journalArticle

@article{e03642d4bb0d432e8062c073047abf9e,
title = "Grubbs carbene complex-catalyzed cleavage of allyl vic-diols to aldehydes with a co-oxidant: Application to the selective cleavage of huge marine molecules",
abstract = "An oxidative cleavage of allyl vic-diols to aldehydes catalyzed by a Grubbs carbene complex using a co-oxidant has been established for the first time, with good yields. The utility of this selective cleavage reaction was demonstrated through the use of two huge marine molecules, symbiodinolide and N-p-BrBz palytoxin.",
keywords = "Catalytic reaction, Degradation reaction, Grubbs carbene complex, Marine huge molecule",
author = "Chunguang Han and Yoshi Yamano and Fumitoshi Kakiuchi and Kazuhiko Nakamura and Daisuke Uemura",
year = "2011",
month = "12",
day = "9",
doi = "10.1016/j.tet.2011.09.002",
language = "English",
volume = "67",
pages = "9622--9626",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "49",

}

TY - JOUR

T1 - Grubbs carbene complex-catalyzed cleavage of allyl vic-diols to aldehydes with a co-oxidant

T2 - Application to the selective cleavage of huge marine molecules

AU - Han, Chunguang

AU - Yamano, Yoshi

AU - Kakiuchi, Fumitoshi

AU - Nakamura, Kazuhiko

AU - Uemura, Daisuke

PY - 2011/12/9

Y1 - 2011/12/9

N2 - An oxidative cleavage of allyl vic-diols to aldehydes catalyzed by a Grubbs carbene complex using a co-oxidant has been established for the first time, with good yields. The utility of this selective cleavage reaction was demonstrated through the use of two huge marine molecules, symbiodinolide and N-p-BrBz palytoxin.

AB - An oxidative cleavage of allyl vic-diols to aldehydes catalyzed by a Grubbs carbene complex using a co-oxidant has been established for the first time, with good yields. The utility of this selective cleavage reaction was demonstrated through the use of two huge marine molecules, symbiodinolide and N-p-BrBz palytoxin.

KW - Catalytic reaction

KW - Degradation reaction

KW - Grubbs carbene complex

KW - Marine huge molecule

UR - http://www.scopus.com/inward/record.url?scp=80555150659&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80555150659&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2011.09.002

DO - 10.1016/j.tet.2011.09.002

M3 - Article

VL - 67

SP - 9622

EP - 9626

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 49

ER -