Radical macrocyclisations in synthesis. A new approach to mukulol and marine cembranolide lactones

Cox, N. J. G.; Pattenden, Gerald; Mills, S. D.

doi:10.1016/s0040-4039(00)95271-7

Cited by 36 publications

(4 citation statements)

References 34 publications

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“…The a,b-unsaturated acyl radical macrocyclisation approach Over several years we have developed and tested the scope of a number of alkyl radical macrocyclisation reactions in the synthesis of natural products, 13 including the cembrane mukulol 14 and the oestrogenic mycotoxin zearalenone. 15 We have also used radical macrocyclisation reactions in tandem with radical transannulation reactions to synthesise a range of polycyclic constructs, especially steroids.…”

Section: Resultsmentioning

confidence: 99%

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Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin

et al. 2005

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Synthetic approaches to the furanocembrane family of natural products, e.g. lophotoxins, pukalides, bipinnatins, based on: i) an intramolecular cyclisation of an alpha,beta-unsaturated acyl radical intermediate into a conjugated enone, and ii) an intramolecular Stille coupling reaction involving a 2-stannylfuran and a vinyl iodide, are described. A total synthesis of bis-deoxylophotoxin , the probable biological precursor to the neurotoxin lophotoxin, isolated from species of the Pacific sea whip Lophogorgia, is then presented.

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Section: Resultsmentioning

confidence: 99%

“…Flash chromatography with 1% diethyl ether in CH 2 Cl 2 as eluant gave the c -hydroxy ester (0. (5), 243 (14), 197 (15), 185 (12), 131 (5), 117 (39), 115 (26), 101 (19), 75 (100), 55 (25), 45 (29).…”

Section: Methodsmentioning

confidence: 99%

Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin

et al. 2005

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“…83 Pattenden has used a 14-endo radical cyclization in his synthesis of mukulol (102) (Scheme 22). 84 The SCHEME 22 4:1 E/Z mukulol allylic iodide 100 was derived from farnesol in four steps, and was reacted with dilute tin hydride to give a 4:1 isomeric mixture of 101 in 40% yield. The partial loss of alkene stereochemistry shows that bond rotation of the intermediate allylic radical occurred faster than radical cyclization.…”

Section: Large Ringsmentioning

confidence: 99%

Radical reactions in natural product synthesis

Jasperse¹,

Curran²,

Fevig³

1991

Chem. Rev.

965

279

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“…inhibitor nakafuran-8 (288b), which has been isolated from, D. fragilis,215 D. etheria,216 and several n u d i b r a n ~h s , ~~~, " ' has been synthesized by a route involving two rearrangement steps and a double ring-enlargement.21s ( + )-Euryfuran(289), which is metabolite of a species of Euryspongia 217 and of Dysideu h e r b a ~e a , ~~~ has been synthesized from the terrestrial natural product royleanone.220 A formal total synthesis of racemic 9isocyanopupukaenane(290), which is a metabolite of a Hawaiian Hymeniacidon species and the nudibranch Phyllidiu ~a r i c o s a , ~~~ has been reported 222. A synthesis of axisonitrile-…”

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confidence: 99%