Catalytic asymmetric access to α,β unsaturated δ-lactones through a vinylogous aldol reaction:: Application to the total synthesis of the Prelog-Djerassi lactone

被引：46

作者：

Bluet, G ^{[1
]}

Bazán-Tejeda, B ^{[1
]}

Campagne, JM ^{[1
]}

机构：

[1] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol0168317

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A one-step catalytic asymmetric access to alpha,beta unsaturated delta -lactones is described, using a vinylogous Mukaiyama-aidol reaction between a gamma -substituted dienolate and various aldehydes in the presence of Carreira catalyst CuF-(S)-tolBinap. This methodology has been further applied to a straightforward access to the Prelog-Djerassi lactone.

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收藏

页码：3807 / 3810

页数：4

相关论文

共 42 条

[1] Catalytic Asymmetric Vinylogous Mukaiyama-aldol (CAVM) reactions: The enolate activation [J].

Bluet, G ;

Campagne, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4293-4298

[2] Catalytic asymmetric vinylogous Mukaiyama (CAVM) reactions: aldehyde activation versus enolate activation [J].

Bluet, G ;

Campagne, JM .

TETRAHEDRON LETTERS, 1999, 40 (30) :5507-5509

[3]

Bluet G, 2000, SYNLETT, P221

[4] A SHORT, CONVERGENT SYNTHESIS OF ARISTOLINDIQUINONE [J].

BOTHA, ME ;

GILES, RGF ;

YORKE, SC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :85-88

[5] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[6] Stereocontrol in organic synthesis using silicon-containing compounds.: A synthesis of the (±)-Prelog-Djerassi lactone [J].

Chow, HF ;

Fleming, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17) :2651-2662

[7]

Christmann M, 2000, ANGEW CHEM INT EDIT, V39, P4364, DOI 10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO

[8]

2-G

[9]

Collett LA, 1998, PROG CH ORG NAT PROD, V75, P181

[10] A short synthesis of the C1-C7 fragment of methymycin by ring-closing olefin metathesis [J].

Cossy, J ;

Bauer, D ;

Bellosta, V .

TETRAHEDRON LETTERS, 1999, 40 (22) :4187-4188

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