ArticleThe Journal of organic chemistry2011
Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.Journal of the American Chemical Society · 2020Article
- Scalable synthesis of enaminones utilizing Gold's reagents.Tetrahedron, asymmetry · 2017Article
- Rearrangements of organic peroxides and related processes.Beilstein journal of organic chemistry · 2016Review
- Total Syntheses of Proposed (±)-Trichodermatides B and C.Tetrahedron letters · 2013Article
- Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.The Journal of organic chemistry · 2013Article
- Gold (III) Chloride-Catalyzed 6-Advanced synthesis & catalysis · 2013Article
- A macrocyclic β-iodoallenolate intermediate is key: synthesis of the ABD core of phomactin A.Organic letters · 2012Article
- Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.Organic letters · 2012Article
- Constructing the Architecturally Distinctive ABD-Tricycle of Phomactin A through an IntramolecularTetrahedron · 2011Article
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Authors and funding
4 authors.
Funding
Abstract
Our struggles and ultimate success in achieving a total synthesis of phomactin A are described. Our strategy features an intramolecular oxa-[3 + 3] annulation to construct its unique ABD-tricyclic manifold. Although the synthesis would constitute a distinctly new approach with the 12-membered D-ring of phomactin A being assembled simultaneously with the 1-oxadecalin at an early stage, the ABD-tricycle represents a unique structural topology that would pose a number of unprecedented challenges. One challenge concerned elaborating this tricycle to have oxygenation at the proper carbon atoms. To overcome this, we would utilize a Kornblum-DeLaMare ring-opening of a peroxide bridge as well as a challenging late-stage 1,3-allylic alcohol transposition. Further, the structural intricacies of the ABD-tricycle were uncovered by a conformational analysis that would be critical for the C5a-homologation.
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