Studies on the total synthesis of disorazole C1.: An advanced macrocycle intermediate

被引：30

作者：

Hillier, MC ^{[1
]}

Price, AT ^{[1
]}

Meyers, AI ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 18期

关键词：

D O I：

10.1021/jo010249e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of protected tetradehydro-(6,6 ' -S)-(14,14 ' -S)-(16,16 ' -R)-disorazole (3), a potential precursor to the natural product disorazole C-1 (1), is described. Key features of this work include (a) an unprecedented sequential 1.5 O --> O silyl rearrangement/Horner-Wadsworth-Emmons reaction used to construct 18, (b) a highly convergent Sonogashira reaction between the dienyl iodide 7 and the alkyne 8 to assemble the dienyne monomeric fragment 5, and (c) the selective cyclization of 5 to give either the cyclic monomer 23 or the dimer 3.

引用

页码：6037 / 6045

页数：9

共 29 条

[11] REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES [J].

FINAN, JM ;

KISHI, Y .

TETRAHEDRON LETTERS, 1982, 23 (27) :2719-2722

[12] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[13] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .31. STEREOSELECTIVE SYNTHESIS OF ERYTHRONOLIDE A BY EXTREMELY EFFICIENT LACTONIZATION BASED ON CONFORMATIONAL ADJUSTMENT AND HIGH ACTIVATION OF SECO-ACID [J].

HIKOTA, M ;

TONE, H ;

HORITA, K ;

YONEMITSU, O .

TETRAHEDRON, 1990, 46 (13-14) :4613-4628

[14] Investigation of a novel sequential 1,5 O→O silyl migration/Horner-Wadsworth-Emmons reaction [J].

Hillier, MC ;

Meyers, AI .

TETRAHEDRON LETTERS, 2001, 42 (31) :5145-5147

[15] The synthesis of the monomeric moiety of disorazole C1 [J].

Hillier, MC ;

Park, DH ;

Price, AT ;

Ng, R ;

Meyers, AI .

TETRAHEDRON LETTERS, 2000, 41 (16) :2821-2824

[16] AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].

IRELAND, RE ;

LIU, LB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899

[17]

JANSEN R, 1994, LIEBIGS ANN CHEM, P759

[18]

JANSEN R, 1998, GESELLSCHAFT BIOTECH

[19] ENANTIOSELECTIVE CHIRAL BORANE-MEDIATED ALDOL REACTIONS OF SILYL KETENE ACETALS WITH ALDEHYDES - NOVEL EFFECT OF THE TRIALKYLSILYL GROUP OF THE SILYL KETENE ACETAL ON THE REACTION COURSE [J].

KIYOOKA, S ;

KANEKO, Y ;

KOMURA, M ;

MATSUO, H ;

NAKANO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2276-2278

[20]

MCCOMSEY DF, 1995, ENCY REAGENTS ORGANI, V4, P2598

← 1 2 3 →