Literature DB >> 28293944

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Zachary G Brill1, Matthew L Condakes1, Chi P Ting1, Thomas J Maimone1.   

Abstract

The pool of abundant chiral terpene building blocks (i.e., "chiral pool terpenes") has long served as a starting point for the chemical synthesis of complex natural products, including many terpenes themselves. As inexpensive and versatile starting materials, such compounds continue to influence modern synthetic chemistry. This review highlights 21st century terpene total syntheses which themselves use small, terpene-derived materials as building blocks. An outlook to the future of research in this area is highlighted as well.

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Year:  2017        PMID: 28293944      PMCID: PMC5638449          DOI: 10.1021/acs.chemrev.6b00834

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  272 in total

Review 1.  Biological activity of the labdane diterpenes.

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Journal:  Planta Med       Date:  1999-02       Impact factor: 3.352

2.  Total synthesis of (+)-quassin.

Authors:  T K Shing; Q Jiang
Journal:  J Org Chem       Date:  2000-10-20       Impact factor: 4.354

3.  Syntheses and stereochemical revision of pseudopterosin G-J aglycon and helioporin E.

Authors:  S E Lazerwith; T W Johnson; E J Corey
Journal:  Org Lett       Date:  2000-07-27       Impact factor: 6.005

4.  Formal synthesis of (+)-phorbol(1).

Authors:  K Lee; J K Cha
Journal:  J Am Chem Soc       Date:  2001-06-13       Impact factor: 15.419

5.  Progress toward the total synthesis of ingenol: construction of the complete carbocyclic skeleton.

Authors:  H Tang; N Yusuff; J L Wood
Journal:  Org Lett       Date:  2001-05-17       Impact factor: 6.005

Review 6.  The biology of ophiobolins.

Authors:  T K Au; W S Chick; P C Leung
Journal:  Life Sci       Date:  2000-07-07       Impact factor: 5.037

7.  Programming Organic Molecules: Design and Management of Organic Syntheses through Free-Radical Cascade Processes.

Authors:  Andrew J. McCarroll; John C. Walton
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-18       Impact factor: 15.336

8.  Total syntheses of optically active 19-norsteroids. (+)-Estr-4-ene-3,17-dione and (+)13 beta-ethylgon-4-ene-3,17-dione.

Authors:  R A Micheli; Z G Hajos; N Cohen; D R Parrish; L A Portland; W Sciamanna; M A Scott; P A Wehrli
Journal:  J Org Chem       Date:  1975-03-21       Impact factor: 4.354

9.  Novel antimycobacterial benzoxazole alkaloids, from the west Indian Sea whip Pseudopterogorgia elisabethae.

Authors:  A D Rodríguez; C Ramírez; I I Rodríguez; E González
Journal:  Org Lett       Date:  1999-08-12       Impact factor: 6.005

10.  Sesquiterpenes from the basidiomycete Omphalotus illudens.

Authors:  T C McMorris; R Lira; P K Gantzel; M J Kelner; R Dawe
Journal:  J Nat Prod       Date:  2000-11       Impact factor: 4.050

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  34 in total

1.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

2.  Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors:  Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-02-11       Impact factor: 15.419

3.  Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

Authors:  Xirui Hu; Andrew J Musacchio; Xingyu Shen; Yujia Tao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

4.  Oxodealkenylative Cleavage of Alkene C(sp3 )-C(sp2 ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.

Authors:  Andrew J Smaligo; Jason Wu; Nikolas R Burton; Allison S Hacker; Aslam C Shaikh; Jason C Quintana; Ruoxi Wang; Changmin Xie; Ohyun Kwon
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-02       Impact factor: 15.336

5.  Total Synthesis of (+)-6-epi-Ophiobolin A.

Authors:  Danny Q Thach; Zachary G Brill; Huck K Grover; Kenneth V Esguerra; Jordan K Thompson; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336

Review 6.  Synthetic biology, combinatorial biosynthesis, and chemo‑enzymatic synthesis of isoprenoids.

Authors:  Alexandra A Malico; Miles A Calzini; Anuran K Gayen; Gavin J Williams
Journal:  J Ind Microbiol Biotechnol       Date:  2020-09-03       Impact factor: 3.346

7.  Synthesis and Study of the Antimalarial Cardamom Peroxide.

Authors:  Xirui Hu; Pharath Lim; Rick M Fairhurst; Thomas J Maimone
Journal:  Tetrahedron       Date:  2018-03-26       Impact factor: 2.457

8.  Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation.

Authors:  Steven W M Crossley; Guanghu Tong; Michael J Lambrecht; Hannah E Burdge; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419

9.  Total Syntheses of Xiamycins A, C, F, H and Oridamycin A and Preliminary Evaluation of their Anti-Fungal Properties.

Authors:  Magnus Pfaffenbach; Ian Bakanas; Nicholas R O'Connor; Jessica L Herrick; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

10.  Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization.

Authors:  Yifeng Chen; David Huang; Yizhou Zhao; Timothy R Newhouse
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-13       Impact factor: 15.336

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