Synthesis of the C1-C13 Tetraenoate Subunit of the Chivosazoles

被引：32

作者：

Paterson, Ian ^{[1
]}

Kan, S. B. Jennifer ^{[1
]}

Gibson, Lisa J. ^{[1
]}

机构：

[1] Univ Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 16期

基金：

英国工程与自然科学研究理事会;

关键词：

CROSS-COUPLING REACTIONS; SORANGIUM-CELLULOSUM; STEREOSELECTIVE HYDROGENOLYSIS; GLIDING BACTERIA; MYXOBACTERIA; 1,1-DIBROMO-1-ALKENES; CONFIGURATION; ANTIBIOTICS; PALMEROLIDE; MACROLIDES;

D O I：

10.1021/ol101630p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using a combination of asymmetric vinylogous Mukaiyama aldol and Stifle cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.

引用

页码：3724 / 3727

页数：4

共 50 条

[1] Synthesis of the C1-C13 Subunit of Spirastrellolides A and B by Prins Cyclization
Sabitha, Gowravaram
Rao, A. Senkara
Yadav, Jhillu S.
SYNTHESIS-STUTTGART, 2010, (03): : 505 - 509
[2] Synthesis of the C1-C13 Fragment of Biselyngbyaside
Sawant, Pramod
Maier, Martin E.
SYNLETT, 2011, (20) : 3002 - 3004
[3] Synthesis of the C1-C13 fragment of (+)-callipeltoside A
Boulard, Lucie
BouzBouz, Samir
Paris, Jean Marc
Cossy, Janine
SYNLETT, 2007, (09) : 1461 - 1463
[4] Synthesis of the C1-C13 Fragment of Mandelalide A
Athe, Sudhakar
Ghosh, Subhash
SYNTHESIS-STUTTGART, 2016, 48 (06): : 917 - 923
[5] Synthesis of the C1-C13 Segment of Poecillastrin C
Clark, Hugh
Hosokawa, Seijiro
SYNLETT, 2024, 35 (13) : 1596 - 1600
[6] Synthesis of the C1-C13 fragment of leucascandrolide A
Crimmins, MT
Carroll, CA
King, BW
ORGANIC LETTERS, 2000, 2 (05) : 597 - 599
[7] Facile synthesis of the C1-C13 fragment of lyngbouilloside
Gebauer, Julian
Arseniyadis, Stellios
Cossy, Janine
SYNLETT, 2008, (05) : 712 - 714
[8] Synthesis of the C1-C13 fragment of eribulin mesylate
Lee, Yoseon
Park, Yongseo
Jung, Heesun
Kim, Seong Take
Sin, Seunghui
Ko, Eunjung
Myeong, In-Soo
Moon, Hyoungwook
Suhl, Chang Heon
Jung, Yunkyung
Jung, Eunim
Lee, Junkyu
Lee, Kee Young
Oh, Chang-Young
Song, Jooyoung
Yoon, Soo Hwan
Kang, Wonjae
Jung, Jaehun
Shin, Hyunik
TETRAHEDRON, 2019, 75 (33) : 4570 - 4576
[9] Stereoselective synthesis of the C1-C13 fragment of bistramide A
Hiebel, Marie-Aude
Pelotier, Beatrice
Piva, Olivier
TETRAHEDRON LETTERS, 2010, 51 (38) : 5091 - 5093
[10] Efficient Synthesis of the C1-C13 Fragment of Bistramide A
Tomas, Loic
Bechet, Thibault
Jeanneau, Erwann
Gueyrard, David
Goekjian, Peter G.
SYNLETT, 2012, (02) : 215 - 218

← 1 2 3 4 5 →