An approach to serrulatane diterpenes via endo-selective conjugate nucleophilic addition to arene-Cr(CO)3 complexes

被引：23

作者：

Dehmel, F ^{[1
]}

Lex, J ^{[1
]}

Schmalz, HG ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 22期

关键词：

D O I：

10.1021/ol026827a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Starting from a nonracemic planar-chiral arene tricarbonyl chromium complex, the serrulatane diterpenoid (+)-20-methoxy-serrulat-14-en-7,8-diol was synthesized in a highly stereoselective fashion. The key step of the synthesis is an endo-selective conjugate nucleophilic addition of lithio-methylphenyl sulfone to a 1-ethylidene-tetralin-Cr(CO)(3) derivative. By employing different substrates and nucleophiles it was shown that the surprising and rather general endo selectivity must result from a unique complex induced proximity effect under participation of the Cr(CO)(3) moiety.

引用

页码：3915 / 3918

页数：4

共 29 条

[1] STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].

BEAK, P ;

MEYERS, AI .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363

[2] Tandem cationic aza-Cope rearrangement-Mannich cyclization approach to the core structure of FR901483 via a bridgehead iminium ion [J].

Brummond, KM ;

Lu, JL .

ORGANIC LETTERS, 2001, 3 (09) :1347-1349

[3] Hydrogen bonding networks and anion coordination in (η6-arene)Cr(CO)3 complexes:: metal carbonyls as hydrogen bond acceptors [J].

Camiolo, S ;

Coles, SJ ;

Gale, PA ;

Hursthouse, MB ;

Mayer, TA ;

Paver, MA .

CHEMICAL COMMUNICATIONS, 2000, (04) :275-276

[4] THE CHEMISTRY OF EREMOPHILA-SPP .16. NEW SERRULATANES FROM EREMOPHILA-SPP [J].

CROFT, KD ;

GHISALBERTI, EL ;

JEFFERIES, PR ;

PROUDFOOT, GM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (09) :1951-1957

[5] CHEMISTRY OF EREMOPHILA SPP .11. ABSOLUTE-CONFIGURATION OF DIHYDROXYSERRULATIC ACID [J].

CROFT, KD ;

GHISALBERTI, EL ;

JEFFERIES, PR ;

STUART, AD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (09) :2079-2083

[6]

DAVIES SG, 1995, COMPREHENSIVE ORGA 2, V12, P979

[7] Unexpected endo selectivity of conjugate nucleophilic addition to an arene-Cr(CO)3 complex:: Enantioselective synthesis of the diterpene 11-epi-helioporin B [J].

Dehmel, F ;

Schmalz, HG .

ORGANIC LETTERS, 2001, 3 (22) :3579-3582

[8]

FORSTER PG, 1986, PHYTOCHEMISTRY, V25, P1477

[9] Preparation of helioporin D from the seco-pseudopterosin aglycone:: Revision of the stereostructure of helioporin D [J].

Geller, T ;

Jakupovic, J ;

Schmalz, HG .

TETRAHEDRON LETTERS, 1998, 39 (12) :1541-1544

[10]

GHISALBERTI EL, 1994, PHYTOCHEMISTRY, V35, P7, DOI 10.1016/S0031-9422(00)90503-X

← 1 2 3 →