Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol

被引：9

作者：

Craig, Donald ^{[1
]}

Funai, Kiyohiko ^{[1
]}

Gore, Sophie J. ^{[1
]}

Kang, Albert ^{[1
]}

Mayweg, Alexander V. W. ^{[2
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] F Hoffmann La Roche Ltd, Div Pharmaceut, CH-4070 Basel, Switzerland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

ALLYLIC TOSYLMALONATE ESTERS; (&/-)-CIS-CHRYSANTHEMIC ACID; REAGENTS; (+)-GRANDISOL; HETEROCYCLES; LACTONES; IRELAND; ROUTE;

D O I：

10.1039/c1ob06619f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unsaturated eight-membered lactones undergo decarboxylative and non-decarboxylative transannular Ireland-Claisen rearrangement reactions, to give substituted vinylcyclobutanes. A formal synthesis of (+/-)-grandisol is described.

引用

页码：8000 / 8002

页数：3

共 50 条

[1] Transannular, decarboxylative Claisen rearrangement reactions for the synthesis of sulfur-substituted vinylcyclopropanes
Craig, Donald
Gore, Sophie J.
Lansdell, Mark I.
Lewis, Simon E.
Mayweg, Alexander V. W.
White, Andrew J. P.
CHEMICAL COMMUNICATIONS, 2010, 46 (27) : 4991 - 4993
[2] FORMAL SYNTHESIS OF (+)-GRANDISOL FROM LEVOGLUCOSENONE
OKANO, K
EBATA, T
KOSEKI, K
KAWAKAMI, H
MATSUMOTO, K
MATSUSHITA, H
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 70 - CARB
[3] FORMAL SYNTHESIS OF (+)-GRANDISOL FROM LEVOGLUCOSENONE
OKANO, K
EBATA, T
KOSEKI, K
KAWAKAMI, H
MATSUMOTO, K
MATSUSHITA, H
CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (05) : 861 - 865
[4] Convenient Formal Synthesis of (+)-Grandisol through Lewis Acid Promoted Enantioselective Pinacolic Rearrangement
Frongia, Angelo
Girard, Christian
Ollivier, Jean
Piras, Pier Paolo
Secci, Francesco
SYNLETT, 2008, (18) : 2823 - 2825
[5] Formal total synthesis of (±)-trichodiene via Claisen rearrangement and Robinson annulation
Jung, Jae-Chul
Jung, Young-Jo
Park, Oee-Sook
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (03): : 293 - 297
[6] Proline Ester Enolate Claisen Rearrangement and Formal Total Synthesis of (-)-Cephalotaxine
Jeon, Hongjun
Chung, Yundong
Kum, Sanghee
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 8080 - 8089
[7] ACYCLIC STEREOCONTROL VIA THE CLAISEN REARRANGEMENT - A FORMAL SYNTHESIS OF (+) TIRANDAMYCIC ACID
ZIEGLER, FE
WESTER, RT
TETRAHEDRON LETTERS, 1984, 25 (06) : 617 - 620
[8] SYNTHESIS OF NOVEL ANNULATED ELLIPTICINES VIA CLAISEN REARRANGEMENT REACTIONS
PLUG, JPM
KOOMEN, GJ
PANDIT, UK
TETRAHEDRON LETTERS, 1992, 33 (16) : 2179 - 2182
[9] USE OF THE KETAL CLAISEN REARRANGEMENT FOR THE SYNTHESIS OF CYCLIC SESQUITERPENES CONTAINING QUATERNARY CENTERS - A FORMAL SYNTHESIS OF CUPARENE
SCHUDA, PF
POTLOCK, SJ
ZIFFER, H
TETRAHEDRON, 1987, 43 (03) : 463 - 468
[10] THE ALICYCLIC CLAISEN-REARRANGEMENT-MEDIATED RING ANNULATION - A FORMAL TOTAL SYNTHESIS OF (+/-)-QUADRONE
FUNK, RL
ABELMAN, MM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 35 - ORGN

← 1 2 3 4 5 →