A convergent enantioselective synthesis of the tetrahydroisoquinoline unit in the spiro ring of ecteinascidin 743

被引：39

作者：

Corey, EJ

Gin, DY

机构：

[1] Dept. of Chem. and Chemical Biology, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 40期

关键词：

D O I：

10.1016/0040-4039(96)01622-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective synthesis of the spiro tetrahydroisoquinoline unit in ecteinascidin 743 is described, employing (+)-tetrahydrocarvone as a readily available and recoverable chiral auxiliary. The synthetic sequence involves a triply-convergent stereoselective bisannulation to construct the tetrahydroisoquinoline framework within 2. Copyright (C) 1996 Elsevier Science Ltd

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页码：7163 / 7166

页数：4

相关论文

共 11 条

[1]

COREY EJ, UNPUB J AM CHEM SOC

[2] TOTAL SYNTHESIS OF (+/-)-SAFRAMYCIN-A [J].

FUKUYAMA, T ;

YANG, L ;

AJECK, KL ;

SACHLEBEN, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3712-3713

[3] STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-SAFRAMYCIN-B [J].

FUKUYAMA, T ;

SACHLEBEN, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) :4957-4958

[4] BIOLOGICALLY-ACTIVE NATURAL-PRODUCTS [J].

RINEHART, KL ;

SAKAI, R ;

HOLT, TG ;

FREGEAU, NL ;

PERUN, TJ ;

SEIGLER, DS ;

WILSON, GR ;

SHIELD, LS .

PURE AND APPLIED CHEMISTRY, 1990, 62 (07) :1277-1280

[5]

RINEHART KL, 1989, TOPICS IN PHARMACEUTICAL SCIENCES 1989, P613

[6] BIOACTIVE COMPOUNDS FROM AQUATIC AND TERRESTRIAL SOURCES [J].

RINEHART, KL ;

HOLT, TG ;

FREGEAU, NL ;

KEIFER, PA ;

WILSON, GR ;

PERUN, TJ ;

SAKAI, R ;

THOMPSON, AG ;

STROH, JG ;

SHIELD, LS ;

SEIGLER, DS ;

LI, LH ;

MARTIN, DG ;

GRIMMELIKHUIJZEN, CJP ;

GADE, G .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (04) :771-792

[7] ECTEINASCIDIN-729, ECTEINASCIDIN-743, ECTEINASCIDIN-745, ECTEINASCIDIN-759A, ECTEINASCIDIN-759B, AND ECTEINASCIDIN-770 - POTENT ANTITUMOR AGENTS FROM THE CARIBBEAN TUNICATE ECTEINASCIDIA-TURBINATA [J].

RINEHART, KL ;

HOLT, TG ;

FREGEAU, NL ;

STROH, JG ;

KEIFER, PA ;

SUN, F ;

LI, LH ;

MARTIN, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4512-4515

[8] SYNTHESIS OF SAFRAMYCINS .3. PREPARATION OF A KEY TRICYCLIC LACTAM INTERMEDIATE TO SAFRAMYCIN-A [J].

SAITO, N ;

YAMAUCHI, R ;

NISHIOKA, H ;

IDA, S ;

KUBO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5391-5395

[9] ADDITIONAL ANTITUMOR ECTEINASCIDINS FROM A CARIBBEAN TUNICATE - CRYSTAL-STRUCTURES AND ACTIVITIES INVIVO [J].

SAKAI, R ;

RINEHART, KL ;

GUAN, Y ;

WANG, AHJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (23) :11456-11460

[10] STUDIES ON THE MOLYBDENUM COFACTOR - AN UNEQUIVOCAL TOTAL SYNTHESIS OF (+/-)-UROTHIONE [J].

TAYLOR, EC ;

REITER, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :285-291