Synthetic Studies of Zoaramine: Construction of the Tetracyclic Skeleton in High Oxidation State

Guoen Wen; Shuo Gu; Jie Chen; Haibing He; Shuanhu Gao

doi:10.1021/acs.orglett.4c04662

Synthetic Studies of Zoaramine: Construction of the Tetracyclic Skeleton in High Oxidation State

Guoen Wen
, Shuo Gu
, Jie Chen
, Haibing He
, Shuanhu Gao^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

We report herein the synthetic studies toward zoaramine, a member of the family of zoaramine-type marine natural products bearing a unique structure. The major synthetic challenge is the stereoselective construction of the congested tetracyclic [6-6-6-6] skeleton in a high oxidation state. Our key strategies are the following: (1) radical cyclization was designed to install the quaternary stereocenters at C-9, C-22, and C-12 as well as formation of the B and D rings; (2) selective oxidations were realized to introduce the functional groups at C-11 and C-24 by using O₂/t-BuOK-promoted hydroxylation and MeReO₃-catalyzed Rubottom oxidation. Our studies reveal a special reactivity and stereocontrol model in the specific chemical environments, which might benefit the related synthetic exploration of this family of natural alkaloids.

Original language	English
Pages (from-to)	2310-2316
Number of pages	7
Journal	Organic Letters
Volume	27
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.4c04662
State	Published - 14 Mar 2025

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title = "Synthetic Studies of Zoaramine: Construction of the Tetracyclic Skeleton in High Oxidation State",

abstract = "We report herein the synthetic studies toward zoaramine, a member of the family of zoaramine-type marine natural products bearing a unique structure. The major synthetic challenge is the stereoselective construction of the congested tetracyclic [6-6-6-6] skeleton in a high oxidation state. Our key strategies are the following: (1) radical cyclization was designed to install the quaternary stereocenters at C-9, C-22, and C-12 as well as formation of the B and D rings; (2) selective oxidations were realized to introduce the functional groups at C-11 and C-24 by using O2/t-BuOK-promoted hydroxylation and MeReO3-catalyzed Rubottom oxidation. Our studies reveal a special reactivity and stereocontrol model in the specific chemical environments, which might benefit the related synthetic exploration of this family of natural alkaloids.",

author = "Guoen Wen and Shuo Gu and Jie Chen and Haibing He and Shuanhu Gao",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

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doi = "10.1021/acs.orglett.4c04662",

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TY - JOUR

T1 - Synthetic Studies of Zoaramine

T2 - Construction of the Tetracyclic Skeleton in High Oxidation State

AU - Wen, Guoen

AU - Gu, Shuo

AU - Chen, Jie

AU - He, Haibing

AU - Gao, Shuanhu

PY - 2025/3/14

Y1 - 2025/3/14

N2 - We report herein the synthetic studies toward zoaramine, a member of the family of zoaramine-type marine natural products bearing a unique structure. The major synthetic challenge is the stereoselective construction of the congested tetracyclic [6-6-6-6] skeleton in a high oxidation state. Our key strategies are the following: (1) radical cyclization was designed to install the quaternary stereocenters at C-9, C-22, and C-12 as well as formation of the B and D rings; (2) selective oxidations were realized to introduce the functional groups at C-11 and C-24 by using O2/t-BuOK-promoted hydroxylation and MeReO3-catalyzed Rubottom oxidation. Our studies reveal a special reactivity and stereocontrol model in the specific chemical environments, which might benefit the related synthetic exploration of this family of natural alkaloids.

AB - We report herein the synthetic studies toward zoaramine, a member of the family of zoaramine-type marine natural products bearing a unique structure. The major synthetic challenge is the stereoselective construction of the congested tetracyclic [6-6-6-6] skeleton in a high oxidation state. Our key strategies are the following: (1) radical cyclization was designed to install the quaternary stereocenters at C-9, C-22, and C-12 as well as formation of the B and D rings; (2) selective oxidations were realized to introduce the functional groups at C-11 and C-24 by using O2/t-BuOK-promoted hydroxylation and MeReO3-catalyzed Rubottom oxidation. Our studies reveal a special reactivity and stereocontrol model in the specific chemical environments, which might benefit the related synthetic exploration of this family of natural alkaloids.

UR - https://www.scopus.com/pages/publications/86000768003

U2 - 10.1021/acs.orglett.4c04662

DO - 10.1021/acs.orglett.4c04662

M3 - 文章

C2 - 40029242

AN - SCOPUS:86000768003

SN - 1523-7060

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SP - 2310

EP - 2316

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Synthetic Studies of Zoaramine: Construction of the Tetracyclic Skeleton in High Oxidation State

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