A formal synthesis of (±) parvifoline by manganese(III)-based oxidative arylation of ketones

被引：15

作者：

Bhowmik, DR ^{[1
]}

Venkateswaran, RV ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Calcutta 700032, W Bengal, India

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 41期

关键词：

oxidative free-radical cyclization; Grob fragmentation; benzocyclooctene;

D O I：

10.1016/S0040-4039(99)01521-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, formal synthesis of the phenolic sesquiterpene (+/-) parvifoline 1 is described involving manganese(III)based oxidative arylation of the ketone 9 as the key step. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：7431 / 7433

页数：3

共 11 条

[1] POLYACETYLENIC COMPOUNDS .243. CONSTITUENTS OF COREOPSIS-PARVIFOLIA BLAKE
BOHLMANN, F
ZDERO, C
[J]. CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (02): : 468 - 473
[2] Cole BM, 1996, J ORG CHEM, V61, P7832
[3] BRIDGED RING-SYSTEMS .16. SYNTHETIC APPROACH TO LYCOPODIUM ALKALOIDS
COLVIN, EW
DOYLE, M
SHROOT, B
RAPHAEL, RA
MARTIN, J
PARKER, W
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (06): : 860 - &
[4] A total synthesis of the racemic sesquiterpene parvifoline
Covarrubias-Zúñiga, A
Cantú, F
Maldonado, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) : 2918 - 2921
[5] SESQUITERPENES FROM PEREZIA-LONGIFOLIA
GARCIA, E
MENDOZA, V
GUZMAN, JA
[J]. JOURNAL OF NATURAL PRODUCTS, 1988, 51 (01): : 150 - 151
[6] TOTAL SYNTHESIS OF (+/-)-PARVIFOLINE
GRIMM, EL
LEVAC, S
COUTU, ML
[J]. TETRAHEDRON LETTERS, 1994, 35 (30) : 5369 - 5372
[7] JOSEPHNATHAN P, 1982, PHYTOCHEMISTRY, V21, P669, DOI 10.1016/0031-9422(82)83162-2
[8] COUMARIN AND TERPENOIDS FROM PEREZIA-ALAMANI VAR OOLEPIS
JOSEPHNATHAN, P
HERNANDEZ, JD
ROMAN, LU
GARCIA, E
MENDOZA, V
MENDOZA, S
[J]. PHYTOCHEMISTRY, 1982, 21 (05) : 1129 - 1132
[9] 2,2-DISUBSTITUTED CYCLOPENTAN-1,3-DIONES .2-1. STUDY OF THE REGIOSELECTIVITY OF ALKYLATION REACTIONS ON 2-METHYL-CYCLOPENTANE-1,3-DIONE
SCHICK, H
SCHWARZ, H
FINGER, A
SCHWARZ, S
[J]. TETRAHEDRON, 1982, 38 (09) : 1279 - 1283
[10] Manganese(III)-based oxidative free-radical cyclizations
Snider, BB
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 339 - 363

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