Total Synthesis of the Proposed Structure of Briarellin J

被引：31

作者：

Crimmins, Michael T. ^{[1
]}

Mans, Mark C. ^{[1
]}

Rodriguez, Abimael D. ^{[2
]}

机构：

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

[2] Univ Puerto Rico, Dept Chem, San Juan, PR 00931 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; CORAL PACHYCLAVULARIA-VIOLACEA; EUNICELLIN-BASED DITERPENOIDS; INDIAN GORGONIAN CORAL; DIELS-ALDER APPROACH; ASBESTINUM PALLAS; NATURAL-PRODUCTS; OPHIRIN-B; STRATEGY;

D O I：

10.1021/ol102169w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

引用

页码：5028 / 5031

页数：4

共 37 条

[1]

Bernardelli P, 1998, HETEROCYCLES, V49, P531

[2] 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

[3] A Unified Strategy for Enantioselective Total Synthesis of Cladiellin and Briarellin Diterpenes: Total Synthesis of Briarellins E and F and the Putative Structure of Alcyonin and Revision of Its Structure Assignment [J].

Corminboeuf, Olivier ;

Overman, Larry E. ;

Pennington, Lewis D. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5458-5470

[4] An intramolecular Diels-Alder strategy for the asbestinins: Enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 [J].

Crimmins, Michael T. ;

Ellis, J. Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1649-1660

[5] An intramolecular Diels-Alder approach to the eunicellins: Enantioselective total syntheses of ophirin B and astrogorgin [J].

Crimmins, MT ;

Brown, BH ;

Plake, HR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1371-1378

[6] Establishing the absolute configuration of the asbestinins: Enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D [J].

Crimmins, MT ;

Ellis, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17200-17201

[7] 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

[8]

Crimmins MT, 2003, HETEROCYCLES, V61, P87

[9] Enantioselective total synthesis of (+)-rogioloxepane A [J].

Crimmins, MT ;

DeBaillie, AC .

ORGANIC LETTERS, 2003, 5 (17) :3009-3011

[10] Ring closing metathesis for the formation of medium ring ethers: the total synthesis of (-)-isolaurallene [J].

Crimmins, MT ;

Emmitte, KA ;

Choy, AL .

TETRAHEDRON, 2002, 58 (10) :1817-1834

← 1 2 3 4 →