Studies towards the synthesis of lindenene:: Unexpected stereochemical outcome of an intramolecular cyclopropanation reaction and synthesis of (±)-epi-Lindenene and (±)-iso-Lindenene

被引：35

作者：

Fenlon, Thomas W. ^{[1
]}

Schwaebisch, Dirk ^{[1
]}

Mayweg, Alexander V. W. ^{[1
]}

Lee, Victor ^{[1
]}

Adlington, Robert M. ^{[1
]}

Baldwin, Jack E. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

SYNLETT | 2007年 / 17期

关键词：

furanosesquiterpene; Hagemann's ester; cyclopropanation; isomerisation; Julia-Kocienski methylenation;

D O I：

10.1055/s-2007-991069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Investigation towards the synthesis of the furanosesquiterpene Lindenene using an intramolecular cyclopropanation reaction gave unexpected ring-junction isomerisation products. These products were elaborated to (+/-)-epi-lindenene and (+/-)-iso-lindenene.

引用

页码：2679 / 2682

页数：4

共 16 条

[1] Improved Julia-Kocienski conditions for the methylenation of aldehydes and ketones
Aïssa, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) : 360 - 363
[2] Danheiser R. L., 1998, ORG SYNTH COLL, VIX, P197
[3] Danheiser R. L., 2003, ORG SYNTH, V80, P160
[4] AN IMPROVED METHOD FOR THE SYNTHESIS OF ALPHA-DIAZO KETONES
DANHEISER, RL
MILLER, RF
BRISBOIS, RG
PARK, SZ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1959 - 1964
[5] Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[6] TOTAL SYNTHESIS OF VARIOUS ELEMANOLIDES
FRIEDRICH, D
BOHLMANN, F
[J]. TETRAHEDRON, 1988, 44 (05) : 1369 - 1392
[7] Stability relationships in bicyclic ketones
Gordon, HL
Freeman, S
Hudlicky, T
[J]. SYNLETT, 2005, (19) : 2911 - 2914
[8] NEW ROUTE FOR SYNTHESIS OF FURAN-DERIVATIVES FROM PROTECTED ALPHA-KETOLS AND KETONES - A TOTAL SYNTHESIS OF FUROVENTALENE
HAGIWARA, H
UDA, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (01): : 91 - 94
[9] TOTAL SYNTHESIS OF (+/-)-ATRACTYLON AND (+/-)-LINDESTRENE
HONAN, MC
[J]. TETRAHEDRON LETTERS, 1985, 26 (51) : 6393 - 6396
[10] TOTAL SYNTHESIS OF STEROID-HORMONES - EFFICIENT STEREOCONTROLLED SYNTHESIS OF 17-METHOXY-6-OXO-D-HOMO-18-NOR-5BETA-ANDROSTA-2,13,15,17-TETRAENE
KAMETANI, T
TSUBUKI, M
NEMOTO, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) : 4391 - 4398

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