(+)-索拉菌素A的全合成。
Total synthesis of (+)-sorangicin A.
作者信息
Smith Amos B, Dong Shuzhi, Brenneman Jehrod B, Fox Richard J
机构信息
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
出版信息
J Am Chem Soc. 2009 Sep 2;131(34):12109-11. doi: 10.1021/ja906115a.
Abstract
The final synthetic challenges associated with (+)-sorangicin A have been overcome, thus leading to the first total synthesis of this complex macrolide antibiotic. Highlights of the highly convergent synthesis include two Julia-Kociénski olefinations to unite three advanced fragments with high E-stereoselectivity. Critical to the final-stage success was the use of a carefully defined Stille coupling and a Mukaiyama macrolactonization as well as Lewis and protic acid-promoted deprotections carefully designed to suppress E/Z isomerization and/or destruction of the delicate (Z,Z,E)-trienoate linkage.
摘要
与（+）-索兰吉星A相关的最终合成挑战已被克服，从而实现了这种复杂大环内酯类抗生素的首次全合成。高度汇聚合成的亮点包括两次Julia-Kociénski烯烃化反应，以高E-立体选择性将三个高级片段连接起来。最终阶段成功的关键在于使用精心设计的Stille偶联反应和Mukaiyama大环内酯化反应，以及精心设计的路易斯酸和质子酸促进的脱保护反应，以抑制E/Z异构化和/或破坏脆弱的（Z,Z,E）-三烯酸酯键。
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本文引用的文献
1
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Org Lett. 2009 Mar 5;11(5):1099-102. doi: 10.1021/ol802942j.
2
Synthesis of the C29-C37 bicyclic ether core of (+)-sorangicin A.
Org Lett. 2006 Sep 14;8(19):4223-5. doi: 10.1021/ol061339e.
3
(+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets.
Org Lett. 2005 Jul 7;7(14):3099-102. doi: 10.1021/ol051119l.
4
Asymmetric synthesis of bicyclic beta-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization: improved efficiency and expanded scope.
J Org Chem. 2005 Apr 1;70(7):2835-8. doi: 10.1021/jo050024u.
5
Structural, functional, and genetic analysis of sorangicin inhibition of bacterial RNA polymerase.
EMBO J. 2005 Feb 23;24(4):674-82. doi: 10.1038/sj.emboj.7600499. Epub 2005 Feb 3.
6
Construction of a C(30-38) dioxabicyclo[3.2.1]octane subtarget for (+)-sorangicin A, exploiting a regio- and stereocontrolled acid-catalyzed epoxide ring opening.
Org Lett. 2004 Apr 29;6(9):1477-80. doi: 10.1021/ol049644s.
7
A cycloaddition cascade approach to the total synthesis of (-)-FR182877.
J Am Chem Soc. 2003 Nov 5;125(44):13531-40. doi: 10.1021/ja037643+.
8
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J Am Chem Soc. 2001 Oct 31;123(43):10772-3. doi: 10.1021/ja016893s.
9
Epothilons A and B: antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria). Production, physico-chemical and biological properties.
J Antibiot (Tokyo). 1996 Jun;49(6):560-3. doi: 10.7164/antibiotics.49.560.
10
The sorangicins, novel and powerful inhibitors of eubacterial RNA polymerase isolated from myxobacteria.
J Antibiot (Tokyo). 1987 Jan;40(1):7-13. doi: 10.7164/antibiotics.40.7.
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