Total synthesis of (+)-strictifolione

被引：53

作者：

BouzBouz, S ^{[1
]}

Cossy, J ^{[1
]}

机构：

[1] Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 11期

关键词：

D O I：

10.1021/ol034619s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The synthesis of (+)-strictifolione was achieved from 3-phenylproprionaldehyde by using enantioselective allyltitanations to control the stereogenic centers at C6, C4', and C6' and a cross-methathesis to control the configuration of the double bond at C1'-C2'.

引用

页码：1995 / 1997

页数：3

共 21 条

[1] Enantioselective allyltitanation. Application to the synthesis of lactone units related to compactin and mevinolin [J].

Bouzbouz, S ;

Cossy, J .

TETRAHEDRON LETTERS, 2000, 41 (18) :3363-3366

[2] Enantioselective synthesis of syn- and anti-1,3-diols via allyltitanation of unprotected β-hydroxyaldehydes [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2000, 2 (04) :501-504

[3] Cross-metathesis reaction. Generation of highly functionalized olefins from unsaturated alcohols [J].

Cossy, J ;

BouzBouz, S ;

Hoveyda, AH .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :327-332

[4] Passifloricins, polyketides α-pyrones from Passiflora foetida resin [J].

Echeverri, F ;

Arango, V ;

Quiñones, W ;

Torres, F ;

Escobar, G ;

Rosero, Y ;

Archbold, R .

PHYTOCHEMISTRY, 2001, 56 (08) :881-885

[5] STUDIES ON THE BIOCHEMICAL-MECHANISM OF THE NOVEL ANTITUMOR AGENT, CI-920 [J].

FRY, DW ;

BORITZKI, TJ ;

JACKSON, RC .

CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1984, 13 (03) :171-175

[6] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[7] ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].

HAFNER, A ;

DUTHALER, RO ;

MARTI, R ;

RIHS, G ;

ROTHESTREIT, P ;

SCHWARZENBACH, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336

[8] LEPTOMYCIN-A AND LEPTOMYCIN-B NEW ANTI-FUNGAL ANTIBIOTICS .2. STRUCTURE ELUCIDATION [J].

HAMAMOTO, T ;

SETO, H ;

BEPPU, T .

JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :646-650

[9] NOVEL ANTITUMOR AGENTS CI-920, PD 113270, AND PD 113271 .3. STRUCTURE DETERMINATION [J].

HOKANSON, GC ;

FRENCH, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (04) :462-466

[10] First total synthesis and determination of the absolute configuration of strictifolione, a new 6-(ω-phenylalkenyl)-5,6-dihydro-α-pyrone, isolated from Cryptocarya strictifolia [J].

Juliawaty, LD ;

Watanabe, Y ;

Kitajima, M ;

Achmad, SA ;

Takayama, H ;

Aimi, N .

TETRAHEDRON LETTERS, 2002, 43 (48) :8657-8660

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