Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

Tony K.M. Shing; Hon Chung Tsui

doi:10.1016/0957-4166(94)80168-1

Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

Tony K.M. Shing, Hon Chung Tsui

Department of Chemistry

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

15 Citations (Scopus)

Abstract

D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.

Original language	English
Pages (from-to)	1269-1274
Number of pages	6
Journal	Tetrahedron: Asymmetry
Volume	5
Issue number	7
DOIs	https://doi.org/10.1016/0957-4166(94)80168-1
Publication status	Published - 1994 Jul

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/0957-4166(94)80168-1

Cite this

@article{837841df87ad474685a35d6c57d70f3b,

title = "Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone",

abstract = "D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.",

author = "Shing, {Tony K.M.} and Tsui, {Hon Chung}",

year = "1994",

month = jul,

doi = "10.1016/0957-4166(94)80168-1",

language = "English",

volume = "5",

pages = "1269--1274",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "7",

}

TY - JOUR

T1 - Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

AU - Shing, Tony K.M.

AU - Tsui, Hon Chung

PY - 1994/7

Y1 - 1994/7

N2 - D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.

AB - D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.

UR - http://www.scopus.com/inward/record.url?scp=0027935210&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027935210&partnerID=8YFLogxK

U2 - 10.1016/0957-4166(94)80168-1

DO - 10.1016/0957-4166(94)80168-1

M3 - Article

AN - SCOPUS:0027935210

SN - 0957-4166

VL - 5

SP - 1269

EP - 1274

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 7

ER -

Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this