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Literature DB >> 19924220

A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin core.

Mingji Dai¹, Zhang Wang, Samuel J Danishefsky.

Abstract

We describe here a novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition. The resulting benzoisoxazolines underwent N-O bond reduction-elimination-electrocyclization sequence to furnish a variety of polysubstituted 2H or 2-alkylated-1-benzo-pyrans. The application of this methodology was further demonstrated in the synthesis of the oxa[3.2.1]octene moiety of cortistatin A.

Entities: Chemical Gene

Year: 2008 PMID： 19924220 PMCID： PMC2598426 DOI： 10.1016/j.tetlet.2008.09.019

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

13 in total

1. Flash photolytic generation of ortho-quinone methide in aqueous solution and study of its chemistry in that medium.

Authors: Y Chiang; A J Kresge; Y Zhu
Journal: J Am Chem Soc Date: 2001-08-22 Impact factor: 15.419

2. Asymmetric 1,3-Dipolar Cycloaddition Reactions.

Authors: Kurt V. Gothelf; Karl Anker Jørgensen
Journal: Chem Rev Date: 1998-04-02 Impact factor: 60.622

3. Cortistatins A, B, C, and D, anti-angiogenic steroidal alkaloids, from the marine sponge Corticium simplex.

Authors: Shunji Aoki; Yasuo Watanabe; Mami Sanagawa; Andi Setiawan; Naoyuki Kotoku; Motomasa Kobayashi
Journal: J Am Chem Soc Date: 2006-03-15 Impact factor: 15.419

4. Rapid construction of the cortistatin pentacyclic core.

Authors: Eric M Simmons; Alison R Hardin; Xuelei Guo; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

5. A concise synthesis of the pentacyclic framework of cortistatins.

Authors: Shuji Yamashita; Kentaro Iso; Masahiro Hirama
Journal: Org Lett Date: 2008-07-17 Impact factor: 6.005

6. Total synthesis of (+)-cortistatin A.

Authors: K C Nicolaou; Ya-Ping Sun; Xiao-Shui Peng; Damien Polet; David Y-K Chen
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. An effective enantioselective route to the platensimycin core.

Authors: Gojko Lalic; E J Corey
Journal: Org Lett Date: 2007-10-11 Impact factor: 6.005

8. A concise synthesis of the cortistatin core.

Authors: Mingji Dai; Samuel J Danishefsky
Journal: Tetrahedron Lett Date: 2008-11-17 Impact factor: 2.415

9. The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins.

Authors: Derek T Craft; Benjamin W Gung
Journal: Tetrahedron Lett Date: 2008-10-06 Impact factor: 2.415

10. Synthesis of (+)-cortistatin A.

Authors: Ryan A Shenvi; Carlos A Guerrero; Jun Shi; Chuang-Chuang Li; Phil S Baran
Journal: J Am Chem Soc Date: 2008-05-14 Impact factor: 15.419

20 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes.

Authors: Sarah M Bronner; Joel L Mackey; K N Houk; Neil K Garg
Journal: J Am Chem Soc Date: 2012-08-15 Impact factor: 15.419

10. A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.

Authors: Jessica L Frie; Christopher S Jeffrey; Erik J Sorensen
Journal: Org Lett Date: 2009-12-03 Impact factor: 6.005

A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin core.

1. Flash photolytic generation of ortho-quinone methide in aqueous solution and study of its chemistry in that medium.

2. Asymmetric 1,3-Dipolar Cycloaddition Reactions.

3. Cortistatins A, B, C, and D, anti-angiogenic steroidal alkaloids, from the marine sponge Corticium simplex.

4. Rapid construction of the cortistatin pentacyclic core.

5. A concise synthesis of the pentacyclic framework of cortistatins.

6. Total synthesis of (+)-cortistatin A.

7. An effective enantioselective route to the platensimycin core.

8. A concise synthesis of the cortistatin core.

9. The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins.

10. Synthesis of (+)-cortistatin A.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes.

3. Formal total synthesis of (±)-cortistatin A.

4. Synthetic studies toward (+)-cortistatin A.

5. Total synthesis of (±)-cortistatin J from furan.

6. The Chemistry and Biology of Nakiterpiosin - C-nor-D-Homosteroids.

7. Synthesis of the Cortistatin Pentacyclic Core by Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling.

8. Chemoselectivity: the mother of invention in total synthesis.

9. Synthesis of cortistatins A, J, K and L.

10. A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.