Synthesis of ferrulactone I and its dimer

Cheskis, B. A.; Shpiro, N. A.; Moiseenkov, A. M.

doi:10.1007/bf01168095

Cited by 5 publications

(6 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast, the synthesis of Cheskis et al, which we also carried out, gave 17 in 9.2 % overall yield, only, albeit 81 % were reported. [33] In the final cyclization step the method of Shiina et al [34] proved to be superior to the Corey-Nicolaou process, and 1 was obtained in 25 % yield (Scheme 3). The synthesis material was identical to the natural compound, and this confirmed the presence of ferrulactone with E,E configuration in male P. rapae.…”

Section: Resultsmentioning

confidence: 97%

Aphrodisiac Pheromones from the Wings of the Small Cabbage White and Large Cabbage White Butterflies, Pieris rapae and Pieris brassicae

et al. 2009

View full text Add to dashboard Cite

The small and large cabbage butterflies, Pieris rapae and P. brassicae, are found worldwide and are of considerable economic importance. The composition of the male scent-producing organs present on the wings was investigated. More than 120 components were identified, but only a small portion proved to be male specific. Major components were the known beetle pheromone ferrulactone (1) in P. rapae and its previously unknown larger analogue, brassicalactone (2), in P. brassicae. The latter carries an additional isoprene unit and is closely related to 1. Other components present in larger amounts on male relative to female wings were hexahydrofarnesylacetone (18) and phytol (23). Brassicalactone (2) was fully characterized by synthesis of its various diastereomers by using ring-closing metathesis. A similar approach to ferrulactone (1) failed, presumably because of its smaller ring size. Instead, this compound was synthesized by using a modified literature procedure. The biological activity of the compounds in the extract was tested by coupled gas chromatographic-electroantennographic (GC-EAD) analysis, which showed that both macrolides and the other major components of the wings can be detected by the antennae of the conspecific female butterflies. Other detectable compounds included several alkanes, which are typical constituents of the butterfly cuticula, derivatives of phytol (23) and long-chain secondary alcohols. Finally, bioassays with males showed that the mixture of 1 (P. rapae) or 2 (P. brassicae) together with 18 and 23 applied to freshly eclosed males increased mating success compared to untreated males. Therefore, the two macrolides 1 and 2 are aphrodisiac pheromone components of male small and large cabbage white butterflies, respectively.

show abstract

Section: Resultsmentioning

confidence: 97%

Aphrodisiac Pheromones from the Wings of the Small Cabbage White and Large Cabbage White Butterflies, Pieris rapae and Pieris brassicae

et al. 2009

View full text Add to dashboard Cite

show abstract

“…Another synthesis of 127 in which the key step is a lactonization of a seco acid was reported by Cheskis et al 91 The Claisen rearrangement of allylic alcohol 136 proceeded stereospecifically to furnish the ester 137 in 95% yield as a single (E,E)-isomer (Scheme 25). Removal of THP protecting group followed by ester hydrolysis led the ω-hydroxyacid 134, which was submitted to latonization using BID, similarly to what was previously reported by Oehlschlager et al 90 Moriya et al 92 obtained the ferrulactone (127) in a short fourstep synthesis, also starting from geraniol (Scheme 26).…”

Section: Ferrulactone Imentioning

confidence: 99%

“…60 These lactones exhibit moderate citotoxicity against human solid tumor cell lines. According to the authors, the (+)-topsentolide C 1 (91) and (+)-topsentolide C 2 (92) are suspected to be artefacts formed during the extraction with methanol. Synthetic approaches to these nine-membered lactones were not found in the literature.…”

Section: Topsentolidesmentioning

confidence: 99%

“…Topsentolides A 1 , A 2 , B 1 , B 2 , B 3 , C 1 , and C 2 (86)(87)(88)(89)(90)(91)(92) are oxylipins isolated in 2006 from the marine sponge Topsentia sp. 60 These lactones exhibit moderate citotoxicity against human solid tumor cell lines.…”

Section: Topsentolidesmentioning

confidence: 99%

“…All the syntheses [89][90][91][92] of ferrulactone I (127) described in literature start from geraniol. The first synthesis of 127 was reported in 1983 by Oehlschlager et al, 89 which obtained the cyclic intermediate 132 by intramolecular alkylation of the ω-bromo-geraniol derivative 131.…”

Section: Ferrulactone Imentioning

confidence: 99%

See 2 more Smart Citations

Natural occurrence, biological activities and synthesis of eight-, nine-, and eleven-membered ring lactones

Ferraz¹,

Bombonato²,

Sano³

et al. 2008

Quím. Nova

View full text Add to dashboard Cite

Recebido em 17/1/08; aceito em 7/4/08; publicado na web em 30/4/08 NATURAL OCCURRENCE, BIOLOGICAL ACTIVITIES AND SYNTHESIS OF EIGHT-, NINE-, AND ELEVEN-MEMBERED RING LACTONES. The natural occurrence, biological activities and synthetic approaches to natural eight-, nine-, and elevenmembered lactones is reviewed. These medium ring lactones are grouped according to ring size, and their syntheses are discussed. The structures of some natural products early identified as medium-ring lactones were revised after total synthesis.

show abstract

Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

et al. 2014

View full text Add to dashboard Cite

The enantioselective synthesis of (2R,3R,4E,8E)-3-hydroxy-2,4,8-trimethyldeca-4,8-dienolide (5) by ring-closing metathesis is described. This compound is an analogue of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (4) which is a rare 11-membered lactone produced by the fungus, Botrytis cinerea. Mutasynthetic studies with compound 5 using two mutants of B. cinerea led to the isolation of four new highly oxygenated 11-membered lactones (11-14) in which compound 5 has been stereoselectively epoxidized and hydroxylated at sites that were not easily accessible by classical synthetic chemistry.

show abstract

Synthesis of ferrulactone I and its dimer

Cited by 5 publications

References 8 publications

Aphrodisiac Pheromones from the Wings of the Small Cabbage White and Large Cabbage White Butterflies, Pieris rapae and Pieris brassicae

Aphrodisiac Pheromones from the Wings of the Small Cabbage White and Large Cabbage White Butterflies, Pieris rapae and Pieris brassicae

Natural occurrence, biological activities and synthesis of eight-, nine-, and eleven-membered ring lactones

Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

Contact Info

Product

Resources

About