（-）-4-去乙酰氧基-1-氧代长春多灵的全合成：长春多灵中嵌入核心杂原子的单原子交换
Total synthesis of (-)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline.
作者信息
Boon Byron A, Yu Yi-Yun, Boger Dale L
机构信息
Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037.
出版信息
Tetrahedron. 2021 May 7;87. doi: 10.1016/j.tet.2021.132117. Epub 2021 Mar 29.
Abstract
A concise total synthesis of (-)-4-desacetoxy-1-oxovindoline is disclosed, bearing a single heteroatom exchange in the core structure of the natural product 4-desacetoxyvindoline. Central to the synthesis is powerful oxadiazole intramolecular [4+2]/[3+2] cycloaddition cascade that formed four C-C bonds, created three new rings, and established five contiguous stereocenters about the new formed central 6-membered ring.
摘要
本文公开了(-)-4-去乙酰氧基-1-氧代长春多灵的简洁全合成方法，该方法在天然产物4-去乙酰氧基长春多灵的核心结构中进行了单一杂原子交换。该合成的关键是强大的恶二唑分子内[4+2]/[3+2]环加成串联反应，该反应形成了四个C-C键，生成了三个新环，并在新形成的中心六元环周围建立了五个连续的立体中心。
相似文献
1
Total synthesis of (-)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline.
Tetrahedron. 2021 May 7;87. doi: 10.1016/j.tet.2021.132117. Epub 2021 Mar 29.
2
Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.
J Am Chem Soc. 2006 Aug 16;128(32):10596-612. doi: 10.1021/ja061256t.
3
Total synthesis of natural (+)- [corrected] and ent-(-)-4-desacetoxy-6,7-dihydrovindorosine [corrected] and natural and ent-minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction.
Org Lett. 2005 Feb 17;7(4):741-4. doi: 10.1021/ol050017s.
4
Asymmetric total synthesis of vindoline.
J Am Chem Soc. 2010 Mar 24;132(11):3685-7. doi: 10.1021/ja910695e.
5
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues.
J Am Chem Soc. 2010 Sep 29;132(38):13533-44. doi: 10.1021/ja106284s.
6
Total synthesis of (-)- and ent-(+)-vindoline.
Org Lett. 2005 Sep 29;7(20):4539-42. doi: 10.1021/ol051975x.
7
Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.
Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27.
8
Total Synthesis of (-)-Vindoline and (+)-4-epi-Vindoline Based on a 1,3,4-Oxadiazole Tandem Intramolecular [4 + 2]/[3 + 2] Cycloaddition Cascade Initiated by an Allene Dienophile.
Org Lett. 2015 Nov 6;17(21):5460-3. doi: 10.1021/acs.orglett.5b02818. Epub 2015 Oct 12.
9
Transannular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles: total synthesis of a unique set of vinblastine analogues.
Org Lett. 2013 Oct 18;15(20):5306-9. doi: 10.1021/ol402549n. Epub 2013 Oct 2.
10
Attempted Synthesis of Alkaloids Condensed with Three-Membered Rings.
Molecules. 2018 Oct 9;23(10):2574. doi: 10.3390/molecules23102574.
本文引用的文献
1
Triarylaminium Radical Cation Promoted Coupling of Catharanthine with Vindoline: Diastereospecific Synthesis of Anhydrovinblastine and Reaction Scope.
J Am Chem Soc. 2019 Sep 11;141(36):14349-14355. doi: 10.1021/jacs.9b06968. Epub 2019 Sep 3.
2
Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.
J Org Chem. 2019 Aug 2;84(15):9397-9445. doi: 10.1021/acs.joc.9b00834. Epub 2019 May 23.
3
The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.
J Org Chem. 2017 Dec 1;82(23):11961-11980. doi: 10.1021/acs.joc.7b02088. Epub 2017 Oct 13.
4
Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance.
J Med Chem. 2017 Sep 14;60(17):7591-7604. doi: 10.1021/acs.jmedchem.7b00958. Epub 2017 Aug 31.
5
Total synthesis of a key series of vinblastines modified at C4 that define the importance and surprising trends in activity.
Chem Sci. 2017 Feb 1;8(2):1560-1569. doi: 10.1039/C6SC04146A. Epub 2016 Nov 3.
6
Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer-dimer interface.
Proc Natl Acad Sci U S A. 2016 Aug 30;113(35):9691-8. doi: 10.1073/pnas.1611405113. Epub 2016 Aug 10.
7
Synthesis of a Potent Vinblastine: Rationally Designed Added Benign Complexity.
J Am Chem Soc. 2016 Jul 13;138(27):8376-9. doi: 10.1021/jacs.6b04330. Epub 2016 Jul 1.
8
Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.
Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27.
9
Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties.
Acc Chem Res. 2015 Mar 17;48(3):653-62. doi: 10.1021/ar500400w. Epub 2015 Jan 14.
10
Potent Vinblastine C20' Ureas Displaying Additionally Improved Activity Against a Vinblastine-Resistant Cancer Cell Line.
ACS Med Chem Lett. 2013 Sep 9;4(10):985-8. doi: 10.1021/ml400281w.
Zotero 插件