Total synthesis of (+/-)-2-pupukeanone

被引：30

作者：

Chang, NC

Chang, CK

机构：

[1] Department of Chemistry, National Sun Yat-Sen University, Kaohsiung

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 15期

关键词：

D O I：

10.1021/jo9603338

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of (+/-)-2-pupukeanone (4) is described in which the pupukeanane skeleton is assembled by means of intramolecular cyclization of tosylate 11 and then the attachment of an isopropyl group at the appropriate position of the tricyclic ring system. The key intermediate 11 was constructed. via a sequence begining from readily available ketone 5 and proceeding through bicyclo[3.2.1]ketone 8 by regioselective ring expansion.

引用

页码：4967 / 4970

页数：4

共 17 条

[1] ACETOXYFULVENE SYNTHESIS OF PROSTAGLANDINS .1. SYNTHESIS OF THE COREY ALDEHYDE
BROWN, ED
CLARKSON, R
LEENEY, TJ
ROBINSON, GE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (12): : 1507 - 1511
[2] 9-ISOCYANOPUPUKEANANE, A MARINE INVERTEBRATE ALLOMONE WITH A NEW SESQUITERPENE SKELETON
BURRESON, BJ
SCHEUER, PJ
FINER, J
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) : 4763 - 4764
[3] ANIONIC OXY-COPE REARRANGEMENT OF 2-ENDO-VINYLBICYCLO[2.2.1]HEPT-5-EN-2-OL - A FACILE ROUTE TOWARDS CIS-HYDRINDANONE DERIVATIVES
CHANG, NC
LU, WF
TSENG, CY
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (03) : 182 - 183
[4] THE TOTAL SYNTHESIS OF (+/-)-CAMPHOR AND (+/-)-EPICAMPHORENONE FROM METHYLCYCLOPENTADIENE
CHANG, NC
CHIU, CT
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1993, 40 (04) : 379 - 384
[5] COREY EJ, 1979, TETRAHEDRON LETT, P2745
[6] TOTAL SYNTHESIS OF THE RACEMATE OF THE SESQUITERPENOID MARINE ALLOMONE 9-ISOCYANOPUPUKEANANE
COREY, EJ
BEHFOROUZ, M
ISHIGURO, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) : 1608 - 1609
[7] TOTAL SYNTHESIS OF (+/-)-2-PUPUKEANONE
FRATER, G
WENGER, J
[J]. HELVETICA CHIMICA ACTA, 1984, 67 (07) : 1702 - 1706
[8] A FORMAL TOTAL SYNTHESIS OF (+/-)-9-ISOCYANOPUPUKEANANE
HSIEH, SL
CHIU, CT
CHANG, NC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) : 3820 - 3823
[9] BICYCLO[3.2.1]OCTENONES AS BUILDING-BLOCKS IN NATURAL-PRODUCTS SYNTHESIS .1. FORMAL SYNTHESIS OF (+/-)-MUSSAENOSIDE AND (+/-)-8-EPILOGANIN AGLUCONES
HSU, LF
CHANG, CP
LI, MC
CHANG, NC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) : 4756 - 4757
[10] NEW SYNTHESIS OF SPIROVETIVANES VIA THE SPIRO ACYLOIN INTERMEDIATE
IBUKA, T
HAYASHI, K
MINAKATA, H
ITO, Y
INUBUSHI, Y
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (13): : 1579 - 1584

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