The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry

被引：24

作者：

Hagiwara, H

Sakai, H

Uchiyama, T

Ito, Y

Morita, N

Hoshi, T

Suzuki, T

Ando, M

机构：

[1] Niigata Univ, Grad Sch Sci & Technol, Ikarashi, Niigata 9502181, Japan

[2] Niigata Univ, Fac Engn, Ikarashi, Niigata 9502181, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 05期

关键词：

D O I：

10.1039/b111594b

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The tetracyclic sesquiterpenoid (+)-cyclomyltaylan-5alpha-ol 1 has been synthesized starting from (S)-(+)-Hajos-Wiechert ketone analogue 10 via stereoselective Claisen rearrangement followed by SmI2-promoted reductive cyclisation. Thus, the absolute configuration has been established to be 2R, 3R, 4R, 5S, 6R, 7R (cyclomyltaylane numbering) as depicted in structure 1.

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页码：583 / 591

页数：9

相关论文

共 32 条

[1]

SESQUITERPENOIDS FROM THE LIVERWORT BAZZANIA-JAPONICA [J].

ASAKAWA, Y ;

TOYOTA, M ;

UEDA, A ;

TORI, M ;

FUKAZAWA, Y .

PHYTOCHEMISTRY, 1991, 30 (09) :3037-3040

[2]

NEW AND SELECTIVE REACTIONS AND REAGENTS IN CARBOHYDRATE-CHEMISTRY [J].

BARTON, DHR ;

MOTHERWELL, WB .

PURE AND APPLIED CHEMISTRY, 1981, 53 (01) :15-31

[3]

NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[4]

Connolly JD, 1991, DICT TERPENOIDS

[5]

TOTAL SYNTHESIS OF (+/-)-APHIDICOLIN [J].

COREY, EJ ;

TIUS, MA ;

DAS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (05) :1742-1744

[6]

SAMARIUM(II) IODIDE MEDIATED TRANSFORMATION OF CARBOHYDRATES TO CARBOCYCLES [J].

ENHOLM, EJ ;

TRIVELLAS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6463-6465

[7]

Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: utility of solid state Baeyer-Villiger oxidation [J].

Hagiwara, H ;

Nagatomo, H ;

Kazayama, S ;

Sakai, H ;

Hoshi, T ;

Suzuki, T ;

Ando, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04) :457-459

[8]

Total synthesis of a monocyclofarnesane dinorsesquiterpenoid isolated from mushroom ingested by beetle: Selectivity in solid-state Baeyer-Villiger reaction [J].

Hagiwara, H ;

Nagatomo, H ;

Yoshii, F ;

Hoshi, T ;

Suzuki, T ;

Ando, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2645-2648

[9]

First total synthesis of chapecoderin A: absolute configuration of the natural product [J].

Hagiwara, H ;

Takeuchi, F ;

Hoshi, T ;

Suzuki, T ;

Ando, M .

TETRAHEDRON LETTERS, 2001, 42 (43) :7629-7631

[10]

OPTICALLY PURE (4AS)-(+)- OR (4AR)-(-)-1,4A-DIMETHYL-4,4A,7,8-TETRAHYDRONAPHTHALENE-2,5(3H,6H)-DIONE AND ITS USE IN THE SYNTHESIS OF AN INHIBITOR OF STEROID-BIOSYNTHESIS [J].

HAGIWARA, H ;

UDA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2308-2311

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