First Total Synthesis and Absolute Configuration of (-)-13-Hydroxy-11,12-epoxy-neocembrene

Zhang, Tao; Liu, Zuosheng; Li, Yulin

doi:10.1055/s-2001-11429

Cited by 10 publications

(2 citation statements)

References 10 publications

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“…395 The structure and absolute stereochemistry of (Ϫ)-13-hydroxy-11,12-epoxyneocembrene 628, also isolated from S. trocheliophorum, 396 has been secured by total synthesis. 397 The soft coral S. molle contained the known diterpene lactone sarcophinone 629 398 and the new diastereomer isosarcophinone 630. 399 Both compounds exhibited in vitro antitumour activity.…”

Section: Coelenteratesmentioning

confidence: 99%

Marine natural products

et al. 2002

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This review covers the literature published in 2001 for marine natural products, with 497 citations (373 for the period January to December 2001) and includes 793 compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates and echinoderms. The emphasis is on new compounds and new stereochemical assignments (683 for 2001), together with relevant biological activities, source organisms and country of origin. Syntheses that confirm or revise structures or stereochemistries have been included (95), including any first total synthesis of a marine natural product.

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Section: Coelenteratesmentioning

confidence: 99%

Marine natural products

et al. 2002

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“…270 Twelve-membered-ring formation is applied to the total synthesis of verticillene (128), a biogenetic precursor of taxane alkaloids. 271,272 The intramolecular cyclization of keto aldehydes for 14-membered-ring formation is used often in the synthesis of many cembrenoide diterpenes such as (±)-cembrene-A, 273 cembrene-C (129), 274 -276 (+)-3,4-epoxycembrene-A, 277,278 (+)-11,12-epoxycembrene-C 279 and its 11,12-dehydro derivative, 280 (-)- 281 and (±)- 282 13-hydroxyneocembrene (130), (-)-13-hydroxy-11,12-epoxy-neocembrene (131), 283 (±)-sarcophytols A and B, 284 (±)-sarcophytol A benzyl ether, 285 (±)-isosarcophytols A, 280 and (±)-crassin acetate methyl ether. 286 Synthesis of the marine cembranoid, (-)-1,3,11-cemratrien-6-ones, 287 preverecynarmin, 288 14-deoxycrassin, 289 pseudoplexaural (132), 289 lepidozene, 267 and bicyclogermacrene 267 have been achieved via 14-membered-ring construction by the McMurry coupling.…”

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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The McMurry coupling reaction has been recognized as one of the most efficient methods for the synthesis of alkenes from carbonyl compounds. This reaction can be applied to the preparation of various alkenes that are otherwise difficult to prepare. For example, sterically congested tetrasubstituted alkenes as well as medium to large membered rings involving natural products may be accessed via this process. This coupling utilizes various low‐valent titanium reagents generated by the reduction of titanium (III or IV) chloride with K, Zn, LiAlH 4 , C 8 K, amongst others. Furthermore, a variety of low‐valent metal species other than titanium, including aluminum, zirconium, niobium, molybdenum, indium, tungsten, and samarium, have also been found to promote the reductive coupling of carbonyl compounds. The scope and limitations of these reagent systems are reviewed in this chapter, together with the stereochemistry and reaction mechanism. This reaction is categorized into four coupling modes: i) homocoupling giving symmetrical alkenes, ii) mixed coupling giving unsymmetrical alkenes, iii) intramolecular coupling giving cycloalkenes, and iv) tandem coupling giving cyclic polyenes. Characteristics of these reaction modes are described briefly. A selection of synthetic applications are reviewed, including examples of the preparation of sterically congested and strained alkenes, medium to large‐ring compounds, biologically active targets, as well as substrates applicable in material science. Experimental conditions used for this versatile process are summarized to assist the choice of suitable conditions.

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Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

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The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

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First Total Synthesis and Absolute Configuration of (-)-13-Hydroxy-11,12-epoxy-neocembrene

Cited by 10 publications

References 10 publications

Marine natural products

Marine natural products

The McMurry Coupling and Related Reactions

Desulfonylation Reactions

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