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

[31] New synthetic methodology to prepare polyfunctionalized heptane building blocks with four stereocenters:: synthesis of the (±)-C17-C23 subunit of Ionomycin
Montaña, AM
García, F
Grima, PM
TETRAHEDRON LETTERS, 1999, 40 (07) : 1375 - 1378
[32] Stereo selective synthesis of C3-C12 fragment of iriomoteolide-1a
Sharma, Gangavaram V. M.
Rajender, Karnekanti
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2018, 22 (02) : 165 - 172
[33] Synthesis of the C1-C21 southern hemisphere of the originally proposed structure of spirastrellolide a
Paterson, I
Anderson, EA
Dalby, SM
SYNTHESIS-STUTTGART, 2005, (19): : 3225 - 3228
[34] Synthesis of C1-C15 of palmerolide A: tactical advances that can lead to better design strategies for polyketide synthesis
Batsomboon, Paratchata
Dudley, Gregory B.
TETRAHEDRON LETTERS, 2016, 57 (33) : 3757 - 3759
[35] Determination of the relative configuration of the C-19 to C-29 fragment of amycin B by 1H and 13C NMR investigations
Hoyer, F
Habermehl, G
Duddeck, H
Tóth, G
MAGNETIC RESONANCE IN CHEMISTRY, 1999, 37 (05) : 371 - 375
[36] Synthesis of the C1-C18 Fragment of Rhizopodin: Late-State Introduction of the Oxazole
Bender, Tobias
Loits, Darran
White, Jonathan M.
Rizzacasa, Mark A.
ORGANIC LETTERS, 2014, 16 (05) : 1450 - 1453
[37] TOTAL SYNTHESIS OF MYXOVIRESCINS .2. ASSEMBLY OF THE NORTHWESTERN PART [C(15)-C(28)]
SEFKOW, M
NEIDLEIN, A
SOMMERFELD, T
STERNFELD, F
MAESTRO, MA
SEEBACH, D
LIEBIGS ANNALEN DER CHEMIE, 1994, (07): : 719 - 729
[38] Studies on Synthesis of the C-1 to C-18 Fragment of Pamamycins 607 and 621A
Ren Guobao
Wu Yikang
CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (09) : 1651 - 1659
[39] 1H and 13C NMR study of a series of C-9-substituted 19-norsteroids
Dallery, L
Bertigny, JP
Doussot, J
Garreau, R
Guy, A
Platzer, N
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2002, 15 (01) : 14 - 20
[40] Asymmetric synthesis of phorboxazole B -: Part I:: Synthesis of the C20-C38 and C39-C46 subunits
Evans, DA
Cee, VJ
Smith, TE
Fitch, DM
Cho, PS
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (14) : 2533 - +

← 1 2 3 4 5 →