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Literature DB >> 20521835

A synthesis of the carbocyclic core of maoecrystal V.

Kiel E Lazarski¹, Dennis X Hu, Charlotte L Stern, Regan J Thomson.

Abstract

An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.

Entities: CellLine Chemical Disease Gene

Mesh：

Substances：
Diterpenes
maoecrystal V

Year: 2010 PMID： 20521835 PMCID： PMC2896894 DOI： 10.1021/ol101025r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

5 in total

1. Synthetic Studies towards Maoecrystal V.

Authors: Feng Peng; Maolin Yu; Samuel J Danishefsky
Journal: Tetrahedron Lett Date: 2009-11-25 Impact factor: 2.415

2. Synthetic study toward the total synthesis of maoecrystal V.

Authors: Jianxian Gong; Guang Lin; Chuang-chuang Li; Zhen Yang
Journal: Org Lett Date: 2009-11-05 Impact factor: 6.005

3. Synthesis of functionalized maoecrystal V core structures.

Authors: K C Nicolaou; Lin Dong; Lujiang Deng; Adam C Talbot; David Y-K Chen
Journal: Chem Commun (Camb) Date: 2009-10-23 Impact factor: 6.222

4. Maoecrystal V, cytotoxic diterpenoid with a novel C19 skeleton from Isodon eriocalyx (Dunn.) hara.

Authors: Sheng-Hong Li; Jia Wang; Xue-Mei Niu; Yun-Heng Shen; Hong-Jie Zhang; Han-Dong Sun; Ma-Lin Li; Qin-E Tian; Yang Lu; Peng Cao; Qi-Tai Zheng
Journal: Org Lett Date: 2004-11-11 Impact factor: 6.005

5. A synthesis of the carbon skeleton of maoecrystal V.

Authors: Paul J Krawczuk; Niklas Schöne; Phil S Baran
Journal: Org Lett Date: 2009-11-05 Impact factor: 6.005

5 in total

8 in total

1. Studies toward the synthesis of maoecrystal V.

Authors: Zhenhua Gu; Armen Zakarian
Journal: Org Lett Date: 2011-01-27 Impact factor: 6.005

2. Toward the total synthesis of maoecrystal V: an intramolecular Diels-Alder route to the maoecrystal V pentacyclic core with the appropriate relative stereochemistry.

Authors: Feng Peng; Samuel J Danishefsky
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

A synthesis of the carbocyclic core of maoecrystal V.

1. Synthetic Studies towards Maoecrystal V.

2. Synthetic study toward the total synthesis of maoecrystal V.

3. Synthesis of functionalized maoecrystal V core structures.

4. Maoecrystal V, cytotoxic diterpenoid with a novel C19 skeleton from Isodon eriocalyx (Dunn.) hara.

5. A synthesis of the carbon skeleton of maoecrystal V.

1. Studies toward the synthesis of maoecrystal V.

2. Toward the total synthesis of maoecrystal V: an intramolecular Diels-Alder route to the maoecrystal V pentacyclic core with the appropriate relative stereochemistry.

3. Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

4. Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V.

5. Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

6. Total synthesis of (±)-maoecrystal V.

7. Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.

8. 11-Step Total Synthesis of (-)-Maoecrystal V.