Establishing the absolute configuration of the asbestinins: Enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D

被引：39

作者：

Crimmins, MT ^{[1
]}

Ellis, JM ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 49期

关键词：

D O I：

10.1021/ja056921x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly stereoselective synthesis of 11-acetoxy-4-deoxyasbestinin D (1) has been completed in 26 linear steps. The synthesis hinges on a selective glycolate aldol addition to establish the C-2 stereocenter, a ring-closing metathesis reaction to complete the oxonene, and an intramolecular Diels-Alder cycloaddition to establish the relative configuration at C-1, C-10, and C-14. This initial total synthesis of an asbestinin also serves to confirm the absolute configuration of this subclass of the C-2-C-11-cyclized cembranoid natural products. Copyright © 2005 American Chemical Society.

引用

页码：17200 / 17201

页数：2

共 46 条

[1] Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin A and of the authentic natural sclerophytins A and B [J].

Bernardelli, P ;

Moradei, OA ;

Friedrich, D ;

Yang, J ;

Gallou, F ;

Dyck, BP ;

Doskotch, RW ;

Lange, T ;

Paquette, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9021-9032

[2]

Bernardelli P, 1998, HETEROCYCLES, V49, P531

[3]

Brown H.C, 1975, ORGANIC SYNTHESIS VI

[4] HYDROBORATION .61. DIISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY - IMPROVED PREPARATION AND ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS-DISUBSTITUTED ALKENES [J].

BROWN, HC ;

DESAI, MC ;

JADHAV, PK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5065-5069

[5] Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes [J].

Chai, YH ;

Vicic, DA ;

McIntosh, MC .

ORGANIC LETTERS, 2003, 5 (07) :1039-1042

[6] The magnesium-ene cyclization stereochemically directed by an allylic oxyanionic group and its application to a highly stereoselective synthesis of (±)-matatabiether.: Allylmagnesium compounds by reductive magnesiation of allyl phenyl sulfides [J].

Cheng, D ;

Zhu, SR ;

Yu, ZF ;

Cohen, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (01) :30-34

[7] Enantioselective total synthesis of briarellins E and F: The first total syntheses of briarellin diterpenes [J].

Corminboeuf, O ;

Overman, LE ;

Pennington, LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6650-6652

[8] Total synthesis of the reputed structure of alcyonin and reassignment of its structure [J].

Corminboeuf, O ;

Overman, LE ;

Pennington, LD .

ORGANIC LETTERS, 2003, 5 (09) :1543-1546

[9] An intramolecular Diels-Alder approach to the eunicelins: Enantioselective total synthesis of ophirin B [J].

Crimmins, MT ;

Brown, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10264-10266

[10]

Crimmins MT, 2004, SYNLETT, P1371

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