Concise asymmetric synthesis of (-)-herbertenediol

被引：22

作者：

Kita, Y ^{[1
]}

Futamura, J ^{[1
]}

Ohba, Y ^{[1
]}

Sawama, Y ^{[1
]}

Ganesh, JK ^{[1
]}

Fujioka, H ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(02)02440-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rearrangement of the optically active 3-aryl-2-methyl-2,3-epoxy tosylate (>98% ee) afforded the alpha-keto tosylate with a chiral quaternary carbon center and without loss of chirality. Reductive removal of the tosyloxy group gave the keto compound with a chiral quaternary carbon center, which was converted to (-)-herbertenediol (>98% ee). (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：411 / 413

页数：3

共 27 条

[1] New route to herbertanes via a Suzuki cross-coupling reaction:: synthesis of herbertenediol [J].

Abad, A ;

Agulló, C ;

Cuñat, AC ;

Jiménez, D ;

Perni, RH .

TETRAHEDRON, 2001, 57 (48) :9727-9735

[2] Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B [J].

Bringmann, G ;

Pabst, T ;

Henschel, P ;

Kraus, J ;

Peters, K ;

Peters, EM ;

Rycroft, DS ;

Connolly, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9127-9133

[3] Novel concepts in directed biaryl synthesis - Part 76 - First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol [J].

Bringmann, G ;

Pabst, T ;

Rycroft, DS ;

Connolly, JD .

TETRAHEDRON LETTERS, 1999, 40 (03) :483-486

[4] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS [J].

BURGESS, EM ;

PENTON, HR ;

TAYLOR, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :26-31

[5]

CHAU P, 1987, Proceedings of the National Science Council Republic of China Part A Physical Science and Engineering, V11, P124

[6] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[7]

CRISAN C, 1957, B SOC CHIM FR, P1451

[8] Total syntheses of (-)-herbertenediol, (-)-mastigophorene A, and (-)-mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines [J].

Degnan, AP ;

Meyers, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) :2762-2769

[9] ASYMMETRIC-SYNTHESIS OF CHIRAL SPIROCYCLANES - SELECTIVE FORMATION OF 2-ACYLOXY-1-OXOSPIRO[4.N]ALKANES BY REGIOSELECTIVE AND STEREOSELECTIVE REARRANGEMENT OF ALPHA,BETA-EPOXY ACYLATES IN BICYCLO[N.3.0]ALKANE SYSTEMS [J].

FUJIOKA, H ;

KITAGAKI, S ;

IMAI, R ;

KONDO, M ;

OKAMOTO, S ;

YOSHIDA, Y ;

AKAI, S ;

KITA, Y .

TETRAHEDRON LETTERS, 1995, 36 (18) :3219-3222

[10] Total syntheses of neuroprotective mastigophorenes A and B [J].

Fukuyama, Y ;

Matsumoto, K ;

Tonoi, Y ;

Yokoyama, R ;

Takahashi, H ;

Minami, H ;

Okazaki, H ;

Mitsumoto, Y .

TETRAHEDRON, 2001, 57 (33) :7127-7135

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