First total synthesis of the 4a-methyltetrahydrofluorene diterpenoids (±)-dichroanal B and (±)-dichroanone

被引：76

作者：

Banerjee, M ^{[1
]}

Mukhopadhyay, R ^{[1
]}

Achari, B ^{[1
]}

Banerjee, AK ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Kolkata 700032, W Bengal, India

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035506b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A simple synthesis of the 4a-methyltetrahydrofluorene diterpenoids (+/-)-dichroanal B and (+/-)-dichroanone has been achieved through a common hexahydrofluorenone intermediate obtained via Pd(0)-catalyzed reductive cyclization of a substituted 2-(2-bromobenzyl) methylene cyclohexane.

引用

页码：3931 / 3933

页数：3

共 33 条

[11] CONDENSED CYCLIC AND BRIDGED-RING SYSTEMS .3. REGIOSELECTIVITY AND STEREOSELECTIVITY IN ACID-CATALYZED CYCLIZATIONS OF SUBSTITUTED BENZYLCYCLOHEXANOLS - STEREOCONTROLLED SYNTHESIS OF SOME GEM-CARBOXY-METHYL-SUBSTITUTED HEXAHYDROFLUORENE AND HEXAHYDRO-5,9-METHANOBENZOCYCLO-OCTENE DERIVATIVES [J].

GHATAK, UR ;

CHAKRAVARTY, J ;

DASGUPTA, R ;

CHAKRABORTI, PC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (23) :2438-2445

[12] SYNTHETIC STUDIES DIRECTED TO GIBBERELLINS AND RELATED COMPOUNDS [J].

GHATAK, UR ;

CHAKRAVA.J ;

BANERJEE, AK .

TETRAHEDRON, 1968, 24 (04) :1577-&

[13]

GHATAK UR, 1966, TETRAHEDRON LETT, P2449

[14] SYNTHETIC STUDIES TOWARDS COMPLEX DITERPENOIDS .19. TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-DEOXOFAVELINE, (PLUS-OR-MINUS)-FAVELINE METHYL-ETHER AND (PLUS-OR-MINUS)-FAVELINE [J].

GHOSH, AK ;

MUKHOPADHYAY, C ;

GHATAK, UR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (03) :327-332

[15] NOVEL SYNTHETIC ROUTE TO ANGULARLY FUNCTIONALIZED HYDROFLUORENE DERIVATIVES BY A REGIOSPECIFIC AND STEREOSPECIFIC METALATION-CARBONATION REACTION [J].

GHOSH, S ;

GHATAK, UR .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1486-1490

[16]

Horiguchi Y, 1998, CHEM PHARM BULL, V46, P1356

[17]

Ishibashi H, 1999, SYNLETT, P1286

[18] Regiochemistry in aryl radical cyclization onto methylenecycloalkanes [J].

Ishibashi, H ;

Kobayashi, T ;

Nakashima, S ;

Tamura, O .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9022-9027

[19] Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae) [J].

Iwamoto, M ;

Ohtsu, H ;

Tokuda, H ;

Nishino, H ;

Matsunaga, S ;

Tanaka, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (07) :1911-1921

[20] Rearranged abietane-type diterpenes from Salvia dichroantha [J].

Kawazoe, K ;

Yamamoto, M ;

Takaishi, Y ;

Honda, G ;

Fujita, T ;

Sezik, E ;

Yesilada, E .

PHYTOCHEMISTRY, 1999, 50 (03) :493-497

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