The enantioselective syntheses of bisabolane sesquiterpenes Lepistirone and Cheimonophyllon E

Brocksom, Timothy J.; Zanotto, Paulo R.; Brocksom, Ursula

doi:10.1016/j.tetlet.2005.02.058

Cited by 9 publications

(7 citation statements)

References 11 publications

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“…[5][6][7] Chlorination represents a valuable pathway to produce versatile starting materials that are widely used in synthetic organic chemistry. [8][9][10][11] Chloride compounds can be prepared directly by bubbling molecular chlorine, but the difficulty of handling chlorine gas limits this procedure. 12 Other authors have shown a convenient method for this transformation using solid CO 2 and calcium hypochlorite 13,14 or a combination of Vilsmeier reagent and H 2 O 2 .…”

Section: Introductionmentioning

confidence: 99%

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Boualy¹,

Firdoussi²,

Ali³

et al. 2011

J. Braz. Chem. Soc.

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MoCl 5 é usado como eficiente agente na cloração alílica de olefinas terpênicas na presença de NaOCl como doador de cloro. Vários terpenóides são convertidos aos cloretos de alila correspondentes em moderados a bons rendimentos em condições reacionais brandas e otimizadas. Diferentes precursores de molibdênio são estudados. Dentre eles, MoO 3 fornece bom rendimento, mas depois de um tempo de reação maior.MoCl 5 is applied as efficient agent in allylic chlorination of terpenic olefins in the presence of NaOCl as chlorine donor. Various terpenes are converted to the corresponding allylic chlorides in moderate to good yield under mild and optimized reaction conditions. Different molybdenum precursors are also studied. Among them, MoO 3 gives good yield, but after a longer reaction time.

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Section: Introductionmentioning

confidence: 99%

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Boualy¹,

Firdoussi²,

Ali³

et al. 2011

J. Braz. Chem. Soc.

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“…In the second strategy,t he production of cis-26 took place by the acid-catalyzed rearrangement of (+ +)-trans-2,3-epoxycarane (84)u nder heterogeneous catalysis (Scheme 33). [212,227,228] In the methodology of Cabaj and co-workers, [231] (+ +)-2carene (88)i so xidized with m-CPBA by using CHCl 3 as as olvent. Then, the allylic alcoholi so btainedb yr egioselective isomerization of 84 with as olid catalyst that contains basic and acid groups,a ffording 26 in 51 %o verall yield.…”

Section: Chiralterpene Intermediatesmentioning

confidence: 99%

“…In the second strategy, the production of cis ‐ 26 took place by the acid‐catalyzed rearrangement of (+)‐ trans ‐2,3‐epoxycarane ( 84 ) under heterogeneous catalysis (Scheme 33). [212, 227, 228] …”

Section: Synthesis Of Common Terpene and Aromatic Precursors In The Pmentioning

confidence: 99%

Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes

Aguillón

Leão

Miranda

et al. 2021

Chemistry A European J

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“…A regio-and stereoselective alkylation and epoxidation procedure enabled the synthesis of 3 in six steps with 6.7% overall yield and of 4 in nine steps with 4.3% overall yield. 42 In 1993 Ayer and Cruz reported the structure elucidation of tremulenolide A (5) and its reduced diol derivative tremulenediol A (6) from the fungus Phellinus tremulae. 43 Interested in developing new methods for natural product synthesis, Ashfeld and Martin applied a rhodium-catalysed cyclopropanation, allylation and [5+2]-cycloaddition cascade to afford 5 in 16 steps with 6% overall yield.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Secondary Metabolites from Higher Fungi

Reck

Spiteller

2015

Synthesis

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Higher fungi are a promising source of new bioactive natural products with great structural diversity, ranging from polyketides to terpenoids and alkaloids. Many of these structures are a challenge for synthetic organic chemists who have been inspired to develop new total syntheses. Nevertheless, reviews covering syntheses of fungal natural products are lacking. One aim of this review is to close this gap and to present a selection of more recent syntheses of fungal secondary metabolites from different structural classes. Secondly, this review intends to demonstrate that there are many more motivations for the synthesis of natural products than to confirm a proposed structure or to report the first total synthesis of a new natural product. Thirdly, this review is intended to stimulate the interest of organic chemists in the synthesis of fungal natural products. 1

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The enantioselective syntheses of bisabolane sesquiterpenes Lepistirone and Cheimonophyllon E

Cited by 9 publications

References 11 publications

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes

Synthesis of Secondary Metabolites from Higher Fungi

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