A new entry to Amaryllidaceae alkaloids from carbohydrates:: total synthesis of (+)-vittatine

被引：32

作者：

Bohno, M ^{[1
]}

Imase, H ^{[1
]}

Chida, N ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 09期

关键词：

D O I：

10.1039/b402762k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in I was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton was effectively constructed by intramolecular aminomercuration-demercuration, followed by Chugaev reaction.

引用

页码：1086 / 1087

页数：2

共 37 条

[21] TOTAL SYNTHESES OF (+/-)-CRININE AND (+/-)-BUPHANISINE [J].

MARTIN, SF ;

CAMPBELL, CL .

TETRAHEDRON LETTERS, 1987, 28 (05) :503-506

[22] TOTAL SYNTHESES OF (+/-)-CRININE AND (+/-)-BUPHANISINE [J].

MARTIN, SF ;

CAMPBELL, CL .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3184-3190

[23] Chiral synthesis of the CD ring unit of paclitaxel from D-glucal [J].

Momose, T ;

Setoguchi, M ;

Fujita, T ;

Tamura, H ;

Chida, N .

CHEMICAL COMMUNICATIONS, 2000, (22) :2237-2238

[24] A TOTAL SYNTHESIS OF (+-)-CRININE [J].

MUXFELDT, H ;

SCHNEIDE.RS ;

MOOBERRY.JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (15) :3670-&

[25] Palladium-catalyzed asymmetric allylic substitution of 2-arylcyclohexenol derivatives: Asymmetric total syntheses of (+)-crinamine, (-)-haemanthidine, and (+)-pretazettine [J].

Nishimata, T ;

Sato, Y ;

Mori, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1837-1843

[26] First asymmetric total syntheses of (+)-crinamine, (-)-haemanthidine, and (+)-pretazettine [J].

Nishimata, T ;

Mori, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7586-7587

[27] SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS .12. APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS FOR ALKALOID SYNTHESIS - STEREOSELECTIVE PREPARATION OF CIS-3A-ARYLOCTAHYDROINDOLES AND A NEW SHORT ROUTE TO AMARYLLIDACEAE ALKALOIDS [J].

OVERMAN, LE ;

MENDELSON, LT ;

JACOBSEN, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6629-6637

[28] SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS .14. TOTAL SYNTHESIS OF (-)-CRININE - USE OF TANDEM CATIONIC AZA-COPE REARRANGEMENT MANNICH CYCLIZATIONS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE AMARYLLIDACEAE ALKALOIDS [J].

OVERMAN, LE ;

SUGAI, S .

HELVETICA CHIMICA ACTA, 1985, 68 (03) :745-749

[29] Assembly of 3a-arylperhydroindoles by the intramolecular cycloaddition of 2-azaallyl anions with alkenes.: Total syntheses of (±)-crinine, (±)-6-epicrinine, (-)-amabiline, and (-)-augustamine [J].

Pearson, WH ;

Lovering, FE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3607-3617

[30] PIPERIDINE ALKALOIDS (ALCALOIDES PIPERIDINIQUES) .6. CHIRAL AND STEREOSELECTIVE TOTAL SYNTHESIS OF (-)-DEOXOPROSOPININE AND (-)-DEOXOPROSOPHYLLINE - INTRAMOLECULAR AMINOMERCURATION OF AN EPSILON,ZETA-UNSATURATED AMINE [J].

SAITOH, Y ;

MORIYAMA, Y ;

HIROTA, H ;

TAKAHASHI, T ;

KHUONGHUU, Q .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (02) :488-492

← 1 2 3 4 →