Literature DB >> 20376298

Studies directed toward the synthesis of the massileunicellins. 2.

Yonghai Chai1, Zonghong Mou, Matthias C McIntosh.   

Abstract

The fully substituted hydroisobenzofuran core of the massileunicellins containing 8 contiguous stereocenters was prepared in 12 steps from (S)-(+)-carvone. Noteworthy elements of the synthesis include a one-step oxidative rearrangement/epoxidation, a novel stereoselective directed reduction of a keto diol, and a directed hydrogenation of a congested tetrasubstituted alkene.

Entities:  

Year:  2010        PMID： 20376298      PMCID： PMC3111956          DOI： 10.1016/j.tetlet.2010.02.095

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


  8 in total

1.  Simplexins A-I, eunicellin-based diterpenoids from the soft coral Klyxum simplex.

Authors:  Shwu-Li Wu; Jui-Hsin Su; Zhi-Hong Wen; Chi-Hsin Hsu; Bo-Wei Chen; Chang-Feng Dai; Yao-Haur Kuo; Jyh-Horng Sheu
Journal:  J Nat Prod       Date:  2009-06       Impact factor: 4.050

Review 2.  Strategies for the total synthesis of C2-C11 cyclized cembranoids.

Authors:  J Michael Ellis; Michael T Crimmins
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

3.  A total synthesis of milbemycin G: approaches to the C1-C10-fragment and completion of the synthesis.

Authors:  Simon Bailey; Madeleine Helliwell; Aphiwat Teerawutgulrag; Eric J Thomas
Journal:  Org Biomol Chem       Date:  2005-09-14       Impact factor: 3.876

4.  Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin a and of the authentic natural sclerophytins A and B.

Authors:  P Bernardelli; O M Moradei; D Friedrich; J Yang; F Gallou; B P Dyck; R W Doskotch; T Lange; L A Paquette
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

5.  Total synthesis of milbemycins: a synthesis of (6R)-6-hydroxy-3,4-dihydromilbemycin E.

Authors:  Madeleine Helliwell; Sufia Karim; Emma R Parmee; Eric J Thomas
Journal:  Org Biomol Chem       Date:  2005-09-14       Impact factor: 3.876

6.  Studies directed toward the synthesis of the massileunicellins. 2.

Authors:  Yonghai Chai; Zonghong Mou; Matthias C McIntosh
Journal:  Tetrahedron Lett       Date:  2010-05-05       Impact factor: 2.415

7.  Asymmetric synthesis of (+)-polyanthellin A.

Authors:  Matthew J Campbell; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

8.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005
  8 in total
  5 in total

1.  Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors:  Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal:  J Org Chem       Date:  2011-08-05       Impact factor: 4.354

2.  Studies directed toward the synthesis of the massileunicellins. 2.

Authors:  Yonghai Chai; Zonghong Mou; Matthias C McIntosh
Journal:  Tetrahedron Lett       Date:  2010-05-05       Impact factor: 2.415

3.  Total synthesis of phomactin A.

Authors:  Yu Tang; Kevin P Cole; Grant S Buchanan; Gang Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

4.  Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

Authors:  T David Bateman; Aarti L Joshi; Kwangyul Moon; Elena N Galitovskaya; Meenakshi Upreti; Timothy C Chambers; Matthias C McIntosh
Journal:  Bioorg Med Chem Lett       Date:  2009-10-22       Impact factor: 2.823

Review 5.  Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches.

Authors:  Dario Matulja; Maria Kolympadi Markovic; Gabriela Ambrožić; Sylvain Laclef; Sandra Kraljević Pavelić; Dean Marković
Journal:  Molecules       Date:  2019-12-28       Impact factor: 4.411
  5 in total

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