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Thermal and photochemical mechanisms for cyclobutane formation in bielschowskysin biosynthesis

Tang, Bencan; Simion, Robert; Paton, Robert S.


Bencan Tang

Robert Simion

Robert S. Paton


The unique structure of furanocembranoid natural product bielschowskysin has provoked a number of biosynthetic hypotheses: quantum chemical calculations provide a means to assess the feasibility of postulated mechanisms in the construction of this unusual carbon skeleton. Calculations reveal that thermal closure is possible in water via an unusual concerted cyclobutane-forming transition state without the intervention of an enzyme. Photocycloaddition is computed to be extremely efficient, provided enol ether triplet sensitization can be achieved by an appropriate light source. The possible existence of a stable dicarbonyl intermediate presents a challenge for the thermal route, implicating a photochemical pathway in bielschowskysin biosynthesis.


Tang, B., Simion, R., & Paton, R. S. (in press). Thermal and photochemical mechanisms for cyclobutane formation in bielschowskysin biosynthesis. SYNLETT, 26(4),

Journal Article Type Article
Acceptance Date Jan 14, 2015
Online Publication Date Feb 9, 2015
Deposit Date Oct 19, 2017
Journal Synlett
Print ISSN 0936-5214
Electronic ISSN 1437-2096
Publisher Thieme Publishing
Peer Reviewed Peer Reviewed
Volume 26
Issue 4
Keywords biosynthesis; concerted; cyclization; DFT; transition states
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