A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine

被引：23

作者：

Booker-Milburn, KI ^{[1
]}

Hirst, P ^{[1
]}

Charmant, JPH ^{[1
]}

Taylor, LHJ ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Struct Chem Lab, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 14期

关键词：

asymmetric synthesis; cuprates; lactones; natural products; photocyclization; total synthesis;

D O I：

10.1002/anie.200250507

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4.

引用

页码：1642 / 1644

页数：3

共 19 条

[1]

[Anonymous], 1996, ANGEW CHEM, V108, P968

[2]

Bergner EJ, 2000, EUR J ORG CHEM, V2000, P419, DOI 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO

[3]

2-N

[4] Formal intramolecular [5+2] photocycloaddition reactions of maleimides: A novel approach to the CDE ring skeleton of (-)-cephalotaxine [J].

Booker-Milburn, KI ;

Dudin, LF ;

Anson, CE ;

Guile, SD .

ORGANIC LETTERS, 2001, 3 (19) :3005-3008

[5]

Booker-Milburn KI, 2001, EUR J ORG CHEM, V2001, P1473

[6] TOTAL SYNTHESIS OF DL-STENINE [J].

CHEN, CY ;

HART, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6236-6240

[7] TUBEROSTEMONINE L-G [J].

DAO, CN ;

LUGER, P ;

KY, PT ;

KIM, VN ;

DUNG, NX .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1994, 50 :1612-1615

[8] Total synthesis of (-+)-stenine using the IMDAF cycloaddition of a 2-methylthio-5-amido-substituted furan [J].

Ginn, JD ;

Padwa, A .

ORGANIC LETTERS, 2002, 4 (09) :1515-1517

[9] Vinylogous Mannich reactions. The asymmetric total synthesis of (+)-croomine [J].

Martin, SF ;

Barr, KJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (13) :3299-3300

[10] AN EFFICIENT APPROACH TOWARD PYRROLIDINYLLACTONE SYSTEM CHARACTERISTIC OF THE STEMONA ALKALOIDS - LEWIS-ACID CATALYZED STEREOSELECTIVE REACTION OF N-BENZYLOXYCARBONYL-2-METHOXYPYRROLIDINE WITH 3-METHYL-2-TRIMETHYLSILYLOXYFURAN [J].

MORIMOTO, Y ;

NISHIDA, K ;

HAYASHI, Y ;

SHIRAHAMA, H .

TETRAHEDRON LETTERS, 1993, 34 (36) :5773-5776

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