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Literature DB >> 33635666

From an ent-Estrane, through a nat-Androstane, to the Total Synthesis of the Marine-Derived Δ^8,9-Pregnene (+)-03219A.

Zachary A Shalit¹, Lucas C Valdes¹, Wan Shin Kim¹, Glenn C Micalizio¹.

Abstract

The total synthesis of (+)-03219A, a rare Δ8,9-pregnene isolated from the marine-derived Streptomyces sp. SCSIO 03219, is described that is based on a series of transformations that enable progression from epichlorohydrin to an ent-estrane, then conversion to a nat-androstane, and finally establishment of the natural product target. Key to the success of these studies was implementation of two rearrangement processes to formally invert the quaternary center at C13 and establish the C10 quaternary center.

Entities: Chemical

Mesh：

Substances：

Year: 2021 PMID： 33635666 PMCID： PMC8420867 DOI： 10.1021/acs.orglett.1c00382

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

33 in total

1. A history of significant steroid discoveries and developments originating at the Schering Corporation (USA) since 1948.

Authors: H Herzog; E P Oliveto
Journal: Steroids Date: 1992-12 Impact factor: 2.668

2. Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

Authors: Hem Raj Khatri; Bijay Bhattarai; Will Kaplan; Zhongzheng Li; Marcus John Curtis Long; Yimon Aye; Pavel Nagorny
Journal: J Am Chem Soc Date: 2019-03-14 Impact factor: 15.419

From an ent-Estrane, through a nat-Androstane, to the Total Synthesis of the Marine-Derived Δ^8,9-Pregnene (+)-03219A.

1. A history of significant steroid discoveries and developments originating at the Schering Corporation (USA) since 1948.

2. Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

3. Highlights in steroid chemistry: total synthesis versus semisynthesis.

4. Steroid research at Organon in the golden 1950s and the following years.

5. Asymmetric synthesis of batrachotoxin: Enantiomeric toxins show functional divergence against NaV.

Review 6. Neurosteroids and potential therapeutics: Focus on pregnenolone.

7. Synthetic nat- or ent-steroids in as few as five chemical steps from epichlorohydrin.

8. Steroids, the steroid community, and Upjohn in perspective: a profile of innovation.

9. New strategy for convergent steroid synthesis.

10. Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues.

1. Progress toward the De Novo Asymmetric Synthesis of Euphanes.

2. General Enantioselective and Stereochemically Divergent Four-Stage Approach to Fused Tetracyclic Terpenoid Systems.