Chemical Transformations of the Neoclerodane Diterpenes Eriocephalin and Capitatin:  An Access to 4,5-<i>seco</i>-Neoclerod-5(19)-ene Derivatives

Mössner, Ekkehard; Torre, A.; Rodrı́guez, Benjamı́n

doi:10.1021/np9602170

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Clerodanes1

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1998

2016

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Cited by 7 publications

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“…Some chemical transformations of the clerodanes have been reported including the cleavage of ring A of eriocephalin and capitatin, 54 and the selective reduction 55 and the basecatalysed rearrangement 56 of teucvidin 46 to the ketone 47.…”

Section: Clerodanesmentioning

confidence: 99%

Diterpenoids

Hanson¹

1998

Nat. Prod. Rep.

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Section: Clerodanesmentioning

confidence: 99%

Diterpenoids

Hanson¹

1998

Nat. Prod. Rep.

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Photochemical Transformations of Some Neoclerodane and Labdane Diterpene Ketones

Fontana

Savona²,

Vivona

et al. 1999

European J Organic Chem

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Some neoclerodane (2–4) and labdane (5 and 6) diterpene ketones having a β‐ or γ‐hydroxy function, an α‐epoxy group, or an α‐olefinic double bond have been irradiated at λ = 313 nm in dry solvents (benzene or methanol). Fruticolone (2) yielded the naturally occurring 5,6‐seco‐neoclerodan‐6,1α‐olide derivative fruticolide (1), while hispanolone (5) gave the δ‐lactone 8, both transformations involving a Norrish type I photoreaction. The α,β‐unsaturated ketone derivative 4 was transformed into 7 by a stereoselective intramolecular [2+2] cycloaddition reaction involving its furanic 13(16)‐double bond. Finally, the α‐epoxy ketone 6 was rearranged to the 10(9→8)abeo‐labda‐7,9‐dione derivative 10. Apart from the interest in these reactions for synthetic purposes, the photochemical transformation of fruticolone (2) into fruticolide (1) suggests that the latter might originate from the former as an artefact during the extraction and isolation procedure, rather than from any biogenetic pathway.

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