Enantioselective allyltitanations: synthesis of the proposed structures for passifloricin A

被引：21

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, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(03)01024-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective total synthesis of the proposed structures P1 and P2 for passifloricin A was achieved in 12 steps from n-hexadecanal by using enantioselective allyltitanations and a ring closing metathesis reaction as the key steps. Both PI and P2 are different from passifloricin A. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4471 / 4473

页数：3

共 9 条

[1] 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

[2]

BOUZBOUZ S, 2002, WORKSH NEW MOL HUM H, P44

[3]

COSSY J, 2003, IN PRESS CR ACAD SCI

[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]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[6] 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

[7] Configurational assignment of polyene macrolide antibiotics using the [13C]acetonide analysis [J].

Rychnovsky, SD ;

Rogers, BN ;

Richardson, TI .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :9-17

[8] The development of L2X2Ru=CHR olefin metathesis catalysts:: An organometallic success story [J].

Trnka, TM ;

Grubbs, RH .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (01) :18-29

[9] ON THE USE OF THE O-METHYLMANDELATE ESTER FOR ESTABLISHMENT OF ABSOLUTE-CONFIGURATION OF SECONDARY ALCOHOLS [J].

TROST, BM ;

BELLETIRE, JL ;

GODLESKI, S ;

MCDOUGAL, PG ;

BALKOVEC, JM ;

BALDWIN, JJ ;

CHRISTY, ME ;

PONTICELLO, GS ;

VARGA, SL ;

SPRINGER, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2370-2374

← 1 →