通过丙二烯基乙酸酯与（B）-烷基硼烷之间的偶联实现1,3-二烯的立体选择性组装：两性霉素B1的合成研究
Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.
作者信息
Mandal Amit K, Schneekloth John S, Crews Craig M
机构信息
Department of Chemistry, Yale University, New Haven, CT 06520-8103, USA.
出版信息
Org Lett. 2005 Aug 18;7(17):3645-8. doi: 10.1021/ol051175m.
Abstract
The preparation of three fragments for the total synthesis of amphidinolide B1 has been described. The C16 stereochemistry was set by asymmetric allylic alkylation. C21 and C25 stereogenic centers were set by an enantioselective/diastereoselective double allylation reaction. The C9 configuration was set by an asymmetric heteroene reaction. A differentially substituted stereodefined 1,3-diene iodide was synthesized by iodide-mediated S(N)2' reaction. A novel stereoselective method to assemble a 1,3-diene by coupling an allenic acetate and (B)-alkylborane is also reported. [structure: see text]
摘要
已报道了用于两性霉素B1全合成的三个片段的制备。C16立体化学通过不对称烯丙基烷基化确定。C21和C25立体中心通过对映选择性/非对映选择性双烯丙基化反应确定。C9构型通过不对称杂烯反应确定。通过碘介导的S(N)2'反应合成了一种差异取代的立体定义的1,3-二烯碘化物。还报道了一种通过将烯丙基乙酸酯和(B)-烷基硼烷偶联来组装1,3-二烯的新型立体选择性方法。[结构：见正文]
相似文献
1
Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.通过丙二烯基乙酸酯与（B）-烷基硼烷之间的偶联实现1,3-二烯的立体选择性组装：两性霉素B1的合成研究
Org Lett. 2005 Aug 18;7(17):3645-8. doi: 10.1021/ol051175m.
2
Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.对岩沙海葵毒素B1的合成研究：C9-C26片段的合成
Org Lett. 2005 Sep 15;7(19):4209-12. doi: 10.1021/ol051544e.
3
Asymmetric total synthesis of (-)-amphidinolide V through effective combinations of catalytic transformations.通过催化转化的有效组合对（-）- Amphidinolide V 进行不对称全合成。
J Am Chem Soc. 2013 Apr 10;135(14):5324-7. doi: 10.1021/ja401717b. Epub 2013 Mar 28.
4
Synthetic studies on amphidinolide B1.两性霉素B1的合成研究。
Org Lett. 2006 Feb 2;8(3):427-30. doi: 10.1021/ol052620g.
5
An efficient and stereoselective synthesis of the monomeric counterpart of marinomycin A.高效立体选择性合成马立诺霉素A的单体类似物。
Org Lett. 2007 Apr 12;9(8):1453-6. doi: 10.1021/ol070240k. Epub 2007 Mar 14.
6
Total synthesis and revision of C6 stereochemistry of (+)-amphidinolide W.（+）-两性霉素W的全合成及C6立体化学修正
J Org Chem. 2006 Feb 3;71(3):1085-93. doi: 10.1021/jo052181z.
7
Diastereoselective formation of tetrahydrofurans via Pd-catalyzed asymmetric allylic alkylation: synthesis of the C13-C29 subunit of amphidinolide N.通过钯催化的不对称烯丙基烷基化反应形成四氢呋喃： Amphidinolide N 的 C13-C29 亚基的合成。
Org Lett. 2012 Nov 16;14(22):5632-5. doi: 10.1021/ol302409g. Epub 2012 Oct 25.
8
Stereoselective synthesis of the C1-C29 part of amphidinol 3.两性霉素3中C1 - C29部分的立体选择性合成。
J Org Chem. 2015 Jan 16;80(2):859-71. doi: 10.1021/jo502322m. Epub 2015 Jan 7.
9
Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.合成 Amphidinolide C 的 C(18)-C(34) 片段和 Amphidinolide F 的 C(18)-C(29) 片段。
Org Lett. 2010 Nov 19;12(22):5326-9. doi: 10.1021/ol102345v. Epub 2010 Oct 28.
10
Total synthesis and structural revision of (+)-amphidinolide W.（+）- 扁藻毒素W的全合成及结构修正
J Am Chem Soc. 2004 Mar 31;126(12):3704-5. doi: 10.1021/ja049754u.
引用本文的文献
1
Amphidinolide B: total synthesis, structural investigation, and biological evaluation. Amphidinolide B 的全合成、结构研究与生物评价。
J Org Chem. 2013 Mar 15;78(6):2213-47. doi: 10.1021/jo3026077. Epub 2013 Feb 13.
2
Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.高效合成 Amphidinolide C 和 F 的 C(7)-C(20)亚基。
Org Biomol Chem. 2009 Nov 21;7(22):4582-5. doi: 10.1039/b916744g. Epub 2009 Sep 16.
3
Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2.细胞毒性大环内酯类多球壳菌素B1的全合成及多球壳菌素B2的推测结构
J Am Chem Soc. 2008 Jun 11;130(23):7253-5. doi: 10.1021/ja803012n. Epub 2008 May 20.
4
Synthesis of the C3-C18 fragment of amphidinolides G and H.两性霉素G和H的C3 - C18片段的合成。
Org Lett. 2007 Aug 2;9(16):3001-4. doi: 10.1021/ol071024e. Epub 2007 Jul 7.
5
Synthetic studies on amphidinolide B1.两性霉素B1的合成研究。
Org Lett. 2006 Feb 2;8(3):427-30. doi: 10.1021/ol052620g.
6
Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.对岩沙海葵毒素B1的合成研究：C9-C26片段的合成
Org Lett. 2005 Sep 15;7(19):4209-12. doi: 10.1021/ol051544e.
本文引用的文献
1
Silyl ketone chemistry. Preparation and reactions of silyl allenol ethers. Diels-Alder reaction of siloxy vinylallenes leading to sesquiterpenes.硅基酮化学。硅基烯丙醇醚的制备与反应。硅氧基乙烯基丙二烯的狄尔斯-阿尔德反应合成倍半萜。
J Am Chem Soc. 1986 Nov 1;108(24):7791-800. doi: 10.1021/ja00284a051.
2
Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.通过利用克里明斯（Crimmins）和埃文斯（Evans）羟醛反应中意外的立体化学差异，实现对两性霉素B1、B2和B3的C19 - C26亚基的统一合成。
J Org Chem. 2004 Apr 2;69(7):2569-72. doi: 10.1021/jo035829l.
3
Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.两性霉素，来自共生海洋甲藻的生物活性大环内酯类化合物。
Nat Prod Rep. 2004 Feb;21(1):77-93. doi: 10.1039/b310427n. Epub 2004 Jan 7.
4
Chemistry of potent anti-cancer compounds, amphidinolides.
Curr Med Chem Anticancer Agents. 2001 Aug;1(2):131-49. doi: 10.2174/1568011013354660.
5
Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.使用高度非对映选择性的一锅法双烯丙基硼化反应序列对1,5-反式二醇和1,5-顺式二醇进行对映选择性合成。
J Am Chem Soc. 2002 Nov 20;124(46):13644-5. doi: 10.1021/ja028055j.
6
The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.β-烷基铃木-宫浦交叉偶联反应：发展、机理研究及其在天然产物合成中的应用 文章末尾可找到缩写列表。
Angew Chem Int Ed Engl. 2001 Dec 17;40(24):4544-4568. doi: 10.1002/1521-3773(20011217)40:24<4544::aid-anie4544>3.0.co;2-n.
7
Palladium(II)-catalyzed S(N)2' reactions of alpha-allenic acetates. Stereoconvergent synthesis of (Z,E)-2-bromo-1,3-dienes.
J Org Chem. 2001 Nov 30;66(24):8120-6. doi: 10.1021/jo015950x.
8
Cytotoxic macrolides from a cultured marine dinoflagellate of the genus Amphidinium.
J Nat Prod. 1989 Sep-Oct;52(5):1036-41. doi: 10.1021/np50065a021.
Zotero 插件