Total syntheses of aplysin and debromoaplysin using a diastereoselective, sulfur mediated radical cyclisation strategy

被引：31

作者：

Harrowven, DC ^{[1
]}

Lucas, MC

Howes, PD

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Enzyme Med Chem 2, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 23期

关键词：

terpenes and terpenoids; natural products; radicals and radical reactions; cyclisations; disulfides; oxygen heterocycles;

D O I：

10.1016/S0040-4039(99)00768-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total syntheses of two marine sesquiterpenes, aplysin 1 and debromoaplysin 2, are described. The key step involves a diastereoselective, sulfur mediated radical cyclisation of diene 5 to 7 which simultaneously creates the sterically demanding aplysin skeleton and establishes the relative configuration of the three contiguous stereogenic centres. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4443 / 4444

页数：2

共 25 条

[11] CASCADE RADICAL REACTIONS IN SYNTHESIS - A NEW AND GENERAL-APPROACH TO CONDENSED THIOPHENES [J].

HARROWVEN, DC ;

BROWNE, R .

TETRAHEDRON LETTERS, 1995, 36 (16) :2861-2862

[12] A simple and direct method for converting thioamides into thioesters [J].

Harrowven, DC ;

Lucas, MC ;

Howes, PD .

TETRAHEDRON, 1999, 55 (04) :1187-1196

[13] On the identity of a neo-lignan from the fruits of Virola sebifera [J].

Harrowven, DC ;

Newman, NA ;

Knight, CA .

TETRAHEDRON LETTERS, 1998, 39 (37) :6757-6760

[14] THE REARRANGEMENT OF SOME CYCLOPENTANONE-ARYLOXIMES - SYNTHESIS OF (+/-)-APLYSIN, (+/-)-FILIFORMIN AND OF THEIR DEBROMO ANALOGS [J].

LARONZE, JY ;

ELBOUKILI, R ;

PATIGNY, D ;

DRIDI, S ;

CARTIER, D ;

LEVY, J .

TETRAHEDRON, 1991, 47 (48) :10003-10014

[15] A REMARKABLE SUBSTITUENT EFFECT AN THE ENANTIOSELECTIVITY OF TANDEM ASYMMETRIC EPOXIDATION AND ENANTIOSPECIFIC RING EXPANSION OF CYCLOPROPYLIDENE ALCOHOLS - A NEW ENANTIOCONTROLLED SYNTHESIS OF (-)-DEBROMOAPLYSIN AND (-)-APLYSIN [J].

NEMOTO, H ;

NAGAMOCHI, M ;

ISHIBASHI, H ;

FUKUMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :74-79

[16] A HALOGENATED CHAMIGRANE EPOXIDE AND 6 RELATED HALOGEN-CONTAINING SESQUITERPENES FROM THE RED ALGA LAURENCIA-OKAMURAI [J].

OJIKA, M ;

SHIZURI, Y ;

YAMADA, K .

PHYTOCHEMISTRY, 1982, 21 (09) :2410-2411

[17] TOTAL SYNTHESIS OF (-)-APLYSIN AND (-)-DEBROMOAPLYSIN [J].

RONALD, RC ;

GEWALI, MB ;

RONALD, BP .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2224-2229

[18] KYLINONE, A NEW SESQUITERPENE SKELETON FROM THE MARINE ALGA LAURENCIA-PACIFICA [J].

SELOVER, SJ ;

CREWS, P .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (01) :69-72

[19] LAUREQUINONE, A CYCLOLAURANE SESQUITERPENE FROM THE RED ALGA LAURENCIA-NIDIFICA [J].

SHIZURI, Y ;

YAMADA, A ;

YAMADA, K .

PHYTOCHEMISTRY, 1984, 23 (11) :2672-2673

[20] CHEMICAL CONSTITUENTS OF DIGESTIVE GLAND OF SEA HARE APLYSIA-CALIFORNICA .2. CHEMICAL-TRANSFORMATIONS [J].

STALLARD, MO ;

FAULKNER, DJ .

COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY, 1974, 49 (1B) :37-41

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