Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-Pseudopteroxazole.

@article{Yang2016TotalSO,
  title={Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-Pseudopteroxazole.},
  author={Ming Yang and Xiaowen Yang and Hongbin Sun and Ang Li},
  journal={Angewandte Chemie},
  year={2016},
  volume={55 8},
  pages={
          2851-5
        }
}
The total syntheses of ileabethoxazole, pseudopteroxazole, and seco-pseudopteroxazole, three antituberculosis diterpenoids that had been isolated from Pseudopterogorgia elisabethae, were accomplished in a collective fashion. A cascade alkyne carbopalladation/Stille reaction was exploited to construct a triene precursor with suitable geometry. A fully substituted arene was then assembled through a key 6π electrocyclization/aromatization sequence, and served as an advanced common intermediate… Expand
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References

SHOWING 1-10 OF 95 REFERENCES
Enantiospecific synthesis of the proposed structure of the antitubercular marine diterpenoid pseudopteroxazole: revision of stereochemistry.
An enantiospecific synthesis of structure 1, previously assigned to the antitubercular marine natural product pseudopteroxazole, has been accomplished as outlined in Scheme 1. Coupling of diene acidExpand
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.
TLDR
A concise, enantiospecific synthesis of pseudopteroxazole, which had originally been assigned structure 1, has been accomplished starting from S-(-)-limonene by cationic cyclization to form 14 diastereoselectively and subsequent introduction of the terminal oxazole subunit. Expand
A Direct and Efficient Stereocontrolled Synthetic Route to the Pseudopterosins, Potent Marine Antiinflammatory Agents
Described herein is a new synthetic route to pseudopterosin aglycone (3), a key intermediate for the synthesis of a group of antiinflammatory natural products including pseudopterosin A (1) and EExpand
Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions.
TLDR
This approach has led to a significant reduction in the step count required to access these interesting natural products and demonstrates that cross-conjugated hydrocarbons, erroneously considered by many to be too unstable and difficult to handle, are viable precursors for natural product synthesis. Expand
Benzothiazines in synthesis. A total synthesis of pseudopteroxazole.
TLDR
The synthesis is organized around the use of a stereoselective, intramolecular addition of a sulfoximine carbanion to an alpha,beta-unsaturated ester to form an enantiomerically pure benzothiazine. Expand
Total Synthesis of Epoxyeujindole A.
The total synthesis of epoxyeujindole A, a structurally unusual indole diterpenoid isolated from Eupenicillium javanicum, has been accomplished for the first time. The synthesis features a late-stageExpand
Enantiospecific syntheses of pseudopterosin aglycones. Part 2. Synthesis of pseudopterosin K–L aglycone and pseudopterosin A–F aglycone via a B→BA→BAC annulation strategy
The enantiomeric aglycones of pseudopterosins K–L and A–F are synthesised from (−)- and (+)-isopulegol respectively. Key features are (a) the construction of the C3 stereogenic centre by a directedExpand
Total syntheses of anominine and tubingensin A.
TLDR
A divergent strategy for the total syntheses of the indole terpenoid anominine and its natural congener tubingensin A has been developed and features a radical deoxygenation followed by an efficient side-chain installation. Expand
A general strategy to elisabethane diterpenes: stereocontrolled synthesis of elisapterosin B via oxidative cyclization of an elisabethin precursor.
Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, preparedExpand
Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.
TLDR
A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described and has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods. Expand
...
1
2
3
4
5
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