Literature DB >> 11720581

Nodulisporic acid A synthetic studies. 1. Overall strategy and construction of a western hemisphere subtarget.

A B Smith1, H Ishiyama, Y S Cho, K Ohmoto.   

Abstract

In this, the first of two Letters, we outline our overall strategy for the construction of (+)-nodulisporic acid A (1), a representative member of a new class of indole diterpenes. In addition, we describe the efficient assembly of (-)-6, an advanced western hemisphere subtarget, comprising the ABC rings of (+)-nodulisporic acid A (1). The synthesis proceeded in 9% overall yield (longest linear sequence, 11 steps), exploiting a Shibasaki-Mori tandem transmetalation-cyclization to construct ring B. [reaction: see text]

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Year:  2001        PMID: 11720581     DOI: 10.1021/ol0168871

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


  5 in total

1.  Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

Authors:  Yike Zou; Xiangqin Li; Yun Yang; Simon Berritt; Jason Melvin; Stephen Gonzales; Matthew Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2018-07-20       Impact factor: 15.419

2.  Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.

Authors:  Nicole A Godfrey; Devon J Schatz; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2018-09-28       Impact factor: 15.419

3.  Total Synthesis of (-)-Nodulisporic Acid D.

Authors:  Yike Zou; Jason E Melvin; Stephen S Gonzales; Matthew J Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2015-06-01       Impact factor: 15.419

4.  On the Mechanism of the Asymmetric Aldol Addition of Chiral N-Amino Cyclic Carbamate Hydrazones: Evidence of Non-Curtin-Hammett Behavior.

Authors:  Md Nasir Uddin; John D Knight; Ettore J Rastelli; Chirine Soubra-Ghaoui; Thomas A Albright; Chia-Hua Wu; Judy I Wu; Don M Coltart
Journal:  Chemistry       Date:  2019-10-25       Impact factor: 5.236

5.  Asymmetric synthesis of 2-substituted oxetan-3-ones via metalated SAMP/RAMP hydrazones.

Authors:  Joanna V Geden; Benjamin O Beasley; Guy J Clarkson; Michael Shipman
Journal:  J Org Chem       Date:  2013-11-11       Impact factor: 4.354

  5 in total

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