Synthesis of (+-)-cembrene, a fourteen-membered ring diterpene

Dauben, William G.; Beasley, G. H.; Broadhurst, Max; Muller, B.; Peppard, D. J.; Pesnelle, P.; Suter, C.

doi:10.1021/ja00850a035

Cited by 43 publications

(8 citation statements)

References 14 publications

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“…The combined extracts were then washed with water (20 cm3), dried (MgSO,) and evaporated to yield the crude product mixture as a yellow solid, which was fractionated by column chromatography [Al,O, (neutral, activity, 1,80-200 mesh) hexane-CH2C1, 4: 1). Two compounds were isolated: (1 Z,4E)-1 -anilino-5-phenylpenta-1,4-dien-3-0ne (9, 117 (6), 92 ( 5 ) and 77 (7).…”

Section: Methodsmentioning

confidence: 99%

“…(from EtOH); R, (CH,C12) 0.41; 6,(300 MHz; CDCl,) 1.36 (3 H, t, J 7.l,CH3),4.38(2H,q, J7. (5,4), 9.0 (5, 6e), 3.8 (5, 6a) 3.8 (6a, 5), 3.5 (6a, l), 13.9 (6a, 6e), 3.0 (6a, 8a) 13.9 (6e, 6a), 2.1 (6e, l), 9.0 (6e, 5 ) 11.5 (7, 8a), 5.9 (7, 8e), 2.8 (7,4) 11.5 @a, 7), 4.0 (8a, l), 13.9 (8a, 8e), 3.0 (8a, 6a) 13.9 (8a, 8e), 5.9 (8e, 7) With dimethyl isophthulute 3c. A solution of dimethyl isophthalate (0.16 g, 0.84 mmol) in THF (20 cm3) was added to LVA 2 (1.68 mmol) in THF (20 cm3) at -78 "C and the reaction mixture was left for 2 h. It was then allowed to reach ambient temperature when it was evaporated and the residue was suspended in water (20 cm3).…”

Section: Methodsmentioning

confidence: 99%

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Variable regioselectivity in reactions of N-lithio-N-vinylaniline with arenedicarboxylates and α,β-unsaturated esters

Katritzky¹,

Oniciu²,

Mancheño³

et al. 1994

J. Chem. Soc., Perkin Trans. 1

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Variable regioselectivity in reactions of N-lithio-N-vinylaniline with arenedicarboxylates and α,β-unsaturated esters

Katritzky¹,

Oniciu²,

Mancheño³

et al. 1994

J. Chem. Soc., Perkin Trans. 1

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“…Corey and co-workers have also synthesized non-natural carbon macrocycles up to 18 members in size by both single C–C bond formation and oligomerization. , Macrocyclic lactones are also accessible through this strategy . Humulene has been synthesized a number of times since Corey’s first report, including several alternative approaches by Corey himself. − For the synthesis of other natural products, intramolecular allylic halide coupling has also been employed as a key step in Corey’s total synthesis of d , l -elemol, Dauben’s total synthesis of cembrene, , Pattenden’s total synthesis of casbene, , and (with benzylic halides) Iyoda’s total synthesis of rioccardin B …”

Section: Reductive Halide Couplingmentioning

confidence: 99%

Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis

2017

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First-row transition-metal-mediated reactions constitute an important and growing area of research due to the low cost, low toxicity, and exceptional synthetic versatility of these metals. Currently, there is considerable effort to replace existing precious-metal-catalyzed reactions with first-row analogs. More importantly, there are a plethora of unique transformations mediated by first-row metals, which have no classical second- or third-row counterpart. Herein, the application of first-row metal-mediated methods to the total synthesis of natural products is discussed. This Review is intended to highlight strategic uses of these metals to realize efficient syntheses and highlight the future potential of these reagents and catalysts in organic synthesis.

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“…The reduction of keto esters (23) therefore provides a link between the reduction of ketones (3) and we had hoped to synthesise the corresponding phosphine oxides (32; Z = Ph,PO) by rearrangement of the lactone (30; Z = Ph,PO). However, even after three weeks under reflux in chlorobenzene containing butanol and toluene-psulphonic acid, only 4% of the ester (32; Z = Ph2PO) could be isolated and most of the starting material had been destroyed.…”

Section: )mentioning

confidence: 99%

“…Reactions under phase-transfer conditions (CH2CI2, water, NaOH, tetra-alkylarnmonium salts) also failed. Some reactions gave diphenylphosphonic acid but this was formed by decomposition of ketone (3), not as a result of the Horner-Wittig reaction, as the electrophile was unaffected.…”

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confidence: 99%