Enantioselective total synthesis and assignment of the absolute configuration of (+)-laurokamurene B

Srikrishna, A.; Baire, Beeraiah; Babu, R. Ramesh

doi:10.1016/j.tetasy.2008.02.010

Cited by 21 publications

(5 citation statements)

References 3 publications

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“…311 An enantioselective synthesis from (S)-campholenaldehyde of the sesquiterpene (+)-laurokamurene B, (from Laurencia okamurai Yamada 312 ), established the absolute configuration of laurokamurenes. 313 Three brominated diterpenes 296-298 were isolated from Sphaerococcus coronopifolius (Palaiokastritsa Bay, Corfu Is.) and the structure of the previously reported 299 314 was revised.…”

Section: Green Algaementioning

confidence: 99%

Marine natural products

et al. 2010

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This review covers the literature published in 2008 for marine natural products, with 829 citations (613 for the period January to December 2008) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1065 for 2008), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Green Algaementioning

confidence: 99%

Marine natural products

et al. 2010

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“…Considering that (E)-7-(4-methylstyryl)cyclohepta-1,3,5-triene (2b), the cycloheptatriene required for the preparation of 7h,c an be readily obtained by the treatement of potassium (E)-(4-methylstyryl)trifluoroborate with tropylium tetrafluoroborate in almost quantitative yield, [3] this total synthesis requires just three steps and provides (AE)-10 in 39 %overall yield from commercially available starting materials,w hich compares favorably with previous syntheses of (AE)-10. [17] Cycloaurenones A-C (8a-c)feature a cis-decalin moiety, whereas the dysiherbols (9a-c)s how trans fusion of the A/B rings ( Figure 1). They also differ in their absolute configuration.…”

Section: Entrymentioning

confidence: 99%

Gold(I)‐Catalyzed Synthesis of Indenes and Cyclopentadienes: Access to (±)‐Laurokamurene B and the Skeletons of the Cycloaurenones and Dysiherbols

2017

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The formal (3+ +2) cycloaddition between terminal allenes and aryl or styryl gold(I) carbenes generated by aretroBuchner reaction of 7-substituted 1,3,5-cycloheptatrienesled to indenes and cyclopentadienes,r espectively.T hese cycloaddition processes have been applied to the construction of the carbon skeleton of the cycloaurenones and the dysiherbols as well as to the total synthesis of (AE)-laurokamurene B.

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“…Often members of this class are monocyclic (304)(305)(306)(307)(308)(309)(310)(311)(312)(313)(314)(315)(316)(317)(318)(319)(320), but there are also representatives possessing 6,9-epoxy (321-326), 7,10-epoxy (327 and 328), or 7,11-epoxy (329-350) ring systems, the latter of which are commonly known as caespitanes. Nonetheless, up to now there are 72 bisabolanes and related sesquiterpenes (304-375) identified from Laurencia species and their grazers.…”

Section: Bisabolanes and Related Sesquiterpenesmentioning

confidence: 99%