Total synthesis of (+)-tanikolide via oxidative lactonization

被引：32

作者：

Schomaker, JM ^{[1
]}

Borhan, B ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 04期

关键词：

D O I：

10.1039/b311432e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Tanikolide has been synthesized in eight linear steps with a 31% overall yield. The key step in the synthesis utilizes a recently developed tandem oxidative cleavage-lactonization of a precursor alkenol to deliver the lactone moiety.

引用

页码：621 / 624

页数：4

共 24 条

[1] Methylation ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of Briaran diterpenes [J].

Balasubramaniam, RP ;

Moss, DK ;

Wyatt, JK ;

Spence, JD ;

Gee, A ;

Nantz, MH .

TETRAHEDRON, 1997, 53 (22) :7429-7444

[2] Stereoselective synthesis of (-)-malyngolide, (+)-malyngolide and (+)-tanikolide using ring-closing metathesis [J].

Carda, M ;

Rodríguez, S ;

Castillo, E ;

Bellido, A ;

Díaz-Oltra, S ;

Marco, JA .

TETRAHEDRON, 2003, 59 (06) :857-864

[3] Syntheses of 5-hexadecanolide, 6-acetoxy-5-hexadecanolide and tanikolide [J].

Chang, MY ;

Lin, CL ;

Chen, ST .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2001, 48 (04) :787-794

[4] NUCLEAR MAGNETIC RESONANCE NONEQUIVALENCE OF DIASTEREOMERIC ESTERS OF ALPHA-SUBSTITUTED PHENYLACETIC ACIDS FOR DETERMINATION OF STEREOCHEMICAL PURITY [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (14) :3732-&

[5] A CHEMOENZYMATIC APPROACH TO ENANTIOMERICALLY PURE (R)-2,3-EPOXY-2-(4-PENTENYL)-PROPANOL, AND (S)-2,3-EPOXY-2-(4-PENTENYL)-PROPANOL, A CHIRAL BUILDING BLOCK FOR THE SYNTHESIS OF (R)-FRONTALIN AND (S)-FRONTALIN [J].

FERRABOSCHI, P ;

CASATI, S ;

GRISENTI, P ;

SANTANIELLO, E .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :9-12

[6] Cobalt catalysed hydro-sulfenylation of Michael acceptors [J].

Friend, CL ;

Simpkins, NS ;

Anson, M ;

Polywka, MEC .

TETRAHEDRON, 1998, 54 (12) :2801-2808

[7] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[8]

Kanada RM, 2000, SYNLETT, P1019

[9]

KIRSCHLEGER B, 1986, SYNTHESIS-STUTTGART, P926

[10] D- and L-erythrose as sources of chiral quaternary carbon centers. Total synthesis of (-)-malyngolide and (+)-tanikolide [J].

Koumbis, AE ;

Dieti, KM ;

Vikentiou, MG ;

Gallos, JK .

TETRAHEDRON LETTERS, 2003, 44 (12) :2513-2516

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