Literature DB >> 25871809

A concise synthetic route to the stereotetrad core of the briarane diterpenoids.

Nicholas G Moon1, Andrew M Harned1.   

Abstract

A concise synthesis (under 10 steps) of the stereotetrad core of the briarane diterpenoids is reported. This approach harnesses the unique reactivity of salicylate ester derived 2,5-cyclohexadienones to quickly build complexity. In particular, a highly diastereoselective acetylide conjugate addition/β-ketoester alkylation sequence was used to set the relative configuration of the C1 (quaternary) and C10 (tertiary) vicinal stereocenters. The sterochemical outcome of the β-ketoester alkylation appears to be governed by torsional steering in the transition state.

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Year:  2015        PMID： 25871809      PMCID： PMC5068569          DOI： 10.1021/acs.orglett.5b00816

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


  17 in total

1.  First comprehensive bakkane approach: stereoselective and efficient dichloroketene-based total syntheses of (+/-)- and (-)-9-acetoxyfukinanolide, (+/-)- and (+)-bakkenolide A, (-)-bakkenolides III, B, C, H, L, V, and X, (+/-)- and (-)-homogynolide A, (+/-)-homogynolide B, and (+/-)-palmosalide C.

Authors:  Timothy J Brocksom; Fernando Coelho; Jean-Pierre Deprés; Andrew E Greene; Marco E Freire De Lima; Olivier Hamelin; Benoît Hartmann; Alice M Kanazawa; Yanyun Wang
Journal:  J Am Chem Soc       Date:  2002-12-25       Impact factor: 15.419

2.  New cytotoxic briaran diterpenes from the Formosan gorgonian Briareum sp.

Authors:  J H Sheu; P J Sung; L I Huang; S F Lee; T Wu; B Y Chang; C Y Duh; L S Fang; K Soong; T J Lee
Journal:  J Nat Prod       Date:  1996-10       Impact factor: 4.050

3.  Excavatolides F-M, new briarane diterpenes from the gorgonian Briareum excavatum.

Authors:  P J Sung; J H Su; G H Wang; S F Lin; C Y Duh; J H Sheu
Journal:  J Nat Prod       Date:  1999-03       Impact factor: 4.050

4.  Bioactive diterpenoid containing a reversible "spring-loaded" (E,Z)-dieneone Michael acceptor.

Authors:  Prasoon Gupta; Upasana Sharma; Thomas C Schulz; Eric S Sherrer; Amanda B McLean; Allan J Robins; Lyndon M West
Journal:  Org Lett       Date:  2011-07-12       Impact factor: 6.005

5.  Two-Dimensional NMR Analysis of Acetonide Derivatives in the Stereochemical Assignment of Polyol Chains: The Absolute Configurations of Dermostatins A and B.

Authors:  Scott D. Rychnovsky; Timothy I. Richardson; Bruce N. Rogers
Journal:  J Org Chem       Date:  1997-05-02       Impact factor: 4.354

Review 6.  Diterpenes from gorgonian corals.

Authors:  Fabrice Berrue; Russell G Kerr
Journal:  Nat Prod Rep       Date:  2009-03-25       Impact factor: 13.423

7.  Palladium(0)-catalyzed stereoselective cyclization of allenenes: divergent synthesis of pyrrolidines and 3-azabicyclo[3.1.0]hexanes from single allenenes.

Authors:  Hiroaki Ohno; Yusuke Takeoka; Yoichi Kadoh; Kumiko Miyamura; Tetsuaki Tanaka
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

8.  Diastereoselective zinc-catalyzed conjugate addition of alkynes.

Authors:  Thomas F Knöpfel; Dean Boyall; Erick M Carreira
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

9.  Origin of stereoselectivity of the alkylation of cyclohexadienone-derived bicyclic malonates.

Authors:  Kelly A Volp; Andrew M Harned
Journal:  J Org Chem       Date:  2013-07-25       Impact factor: 4.354

10.  Stereoselective synthesis of quaternary carbons via the dianionic Ireland-Claisen rearrangement.

Authors:  Michael T Crimmins; John D Knight; Philip S Williams; Yan Zhang
Journal:  Org Lett       Date:  2014-04-15       Impact factor: 6.005
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  4 in total

1.  Torsional steering as friend and foe: development of a synthetic route to the briarane diterpenoid stereotetrad.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  Org Biomol Chem       Date:  2017-02-22       Impact factor: 3.876

Review 2.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

Review 3.  Briarane Diterpenoids Isolated from Octocorals between 2014 and 2016.

Authors:  Yin-Di Su; Jui-Hsin Su; Tsong-Long Hwang; Zhi-Hong Wen; Jyh-Horng Sheu; Yang-Chang Wu; Ping-Jyun Sung
Journal:  Mar Drugs       Date:  2017-02-17       Impact factor: 5.118

Review 4.  Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  R Soc Open Sci       Date:  2018-05-23       Impact factor: 2.963
  4 in total

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