A convenient chiron approach to (4R,5R)-5-hydroxyalkylbutan-4-olides and the corresponding 7-oxa analogues from D-(+)-mannitol via an advanced common precursor: syntheses of (-)-muricatacin, 7-oxa-(-)-muricatacin, (4R,5R)-(-)-5-hydroxy-4-decanolide, and (4R,5R)-(-)-7-oxa-5-hydroxy-4-dodecanolide

被引：7

作者：

Chatterjee, Sandip ^{[1
]}

Manna, Avrajit ^{[1
]}

Bhaumik, Tanurima ^{[1
]}

机构：

[1] Jadavpur Univ, Dept Chem, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 24期

关键词：

CONCISE TOTAL-SYNTHESIS; HYDROXYETHYLENE DIPEPTIDE ISOSTERE; HYDROXY-GAMMA-LACTONES; ENANTIOSPECIFIC SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ANNONACEOUS ACETOGENINS; STREPTOMYCES-GRISEUS; NATURAL-PRODUCTS; HIV-1; PROTEASE; RING-CLOSURE;

D O I：

10.1016/j.tetasy.2014.11.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient and concise chiron approach toward the synthesis of (-)-muricatacin and its unnatural 7-oxa analogue starting from commercially available and inexpensive D-(+)-mannitol via an advanced common chiral precursor has been described. In addition, (4R,5R)-(-)-5-hydroxy-4-decanolide and (4R,5R)-(-)-7-oxa-5-hydroxy-4-dodecanolide were also synthesized to show the versatility of this synthetic strategy. The methodology involves the conversion of a common chiral intermediate, prepared from D-(+)-mannitol in six steps, to a variety of target molecules in only two steps. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1624 / 1629

页数：6

共 86 条

[51] Enantiopure hydroxylactones from D-xylose. A novel approach to the enantiodivergent synthesis of (+)- and (-)-muricatacin suitable for the preparation of 7-oxa analogues
Popsavin, V
Krstic, I
Popsavin, M
[J]. TETRAHEDRON LETTERS, 2003, 44 (49) : 8897 - 8900
[52] Design, synthesis and antiproliferative activity of two new heteroannelated (-)-muricatacin mimics
Popsavin, Velimir
Sreco, Bojana
Benedekovic, Goran
Popsavin, Mirjana
Francuz, Jovana
Kojic, Vesna
Bogdanovic, Gordana
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (19) : 5182 - 5185
[53] Enantiodivergent synthesis of muricatacin related lactones from D-xylose based on the latent symmetry concept: preparation of two novel cytotoxic (+)- and (-)-muricatacin 7-oxa analogs
Popsavin, Velimir
Krstic, Ivana
Popsavin, Mirjana
Sreco, Bojana
Benedekovic, Goran
Kojic, Vesna
Bogdanovic, Gordana
[J]. TETRAHEDRON, 2006, 62 (48) : 11044 - 11053
[54] Synthesis and antitumour activity of new muricatacin and goniofufurone analogues
Popsavin, Velimir
Sreco, Bojana
Krstic, Ivana
Popsavin, Mirjana
Kojic, Vesna
Bogdanovic, Gordana
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (10) : 1217 - 1222
[55] SYNTHESIS OF THE HYDROXYETHYLENE DIPEPTIDE ISOSTERE, (2S,4S,5S)-5-AMINO-6-CYCLOHEXYL-4-HYDROXY-2-ISOPROPYL HEXANOIC ACID NORMAL-BUTYL AMIDE
POSS, MA
REID, JA
[J]. TETRAHEDRON LETTERS, 1992, 33 (11) : 1411 - 1414
[56] Enantiospecific synthesis of (-)-muricatacin from L-(+)-tartaric acid
Prasad, Kavirayani R.
Anbarasan, Pazhamalai
[J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (17) : 2465 - 2467
[57] Facile enantiospecific synthesis of (-)-muricatacin
Prasad, Kavirayani R.
Gandi, Vasudevarao
[J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (22) : 2616 - 2619
[58] Concise total synthesis of (-)-muricatacin by tandem ring-closing/cross metathesis
Quinn, KJ
Isaacs, AK
Arvary, RA
[J]. ORGANIC LETTERS, 2004, 6 (23) : 4143 - 4145
[59] INTRAMOLECULAR NUCLEOPHILIC-ADDITION TO PHOTOCHEMICALLY GENERATED KETENES AS A VERSATILE ROUTE TO LACTONES AND LACTAMS - SYNTHESIS OF A MOSQUITO PHEROMONE, GONIOTHALAMIN, ARGENTILACTONE, AND THE STREPTOMYCES L-FACTOR
RAHMAN, SS
WAKEFIELD, BJ
ROBERTS, SM
DOWLE, MD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (05) : 303 - 304
[60] RANGAVAN S, 2003, TETRAHEDRON-ASYMMETR, V14, P101

← 1 2 3 4 5 6 7 8 9 →