ArticleJACS Au2021
DFT Study on the Biosynthesis of Verrucosane Diterpenoids and Mangicol Sesterterpenoids: Involvement of Secondary-Carbocation-Free Reaction Cascades.
Article in JACS Au, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Discovery of UbiA-Type Cyathane Synthases in Bacteria.ACS catalysis · 2025Article
- Article
- Taming nonclassical carbocations to control small ring reactivity.Science advances · 2024Article
- Unprecedented Neoverrucosane and Cyathane Diterpenoids with Anti-Neuroinflammatory Activity from Cultures of the Culinary-Medicinal MushroomMolecules (Basel, Switzerland) · 2023Article
- Article
- Unraveling the role of prenyl side-chain interactions in stabilizing the secondary carbocation in the biosynthesis of variexenol B.Beilstein journal of organic chemistry · 2023Article
- Enzymatic Synthesis of Variediene Analogs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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Authors and funding
6 authors.
Funding
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Abstract
Some experimental observations indicate that a sequential formation of secondary (2°) carbocations might be involved in some biosynthetic pathways, including those of verrucosane-type diterpenoids and mangicol-type sesterterpenoids, but it remains controversial whether or not such 2° cations are viable intermediates. Here, we performed comprehensive density functional theory calculations of these biosynthetic pathways. The results do not support previously proposed pathways/mechanisms: in particular, we find that none of the putative 2° carbocation intermediates is involved in either of the biosynthetic pathways. In verrucosane biosynthesis, the proposed 2° carbocations (
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