Sinularia mayi

Beechan, C.M. Djaassi, C. Eggert, H. (1978) The sesquiterpenes from the soft coral Sinularia mayi. Tetrahedron, 34,2503-8. 

Sarcophytonin B (67) was first isolated from Sarcophyton spp. by Kobayashi and Hirase in 1990. cis- and trarw-Cembranolides were isolated from Sinularia mayi by Uchio et al. (Scheme 6-33). and from Lobophytum michaelae by Coll et al. Cembranolides were assumed to be logical biosynthetic precursors of sarcophytonin B. Several syntheses of the cembranolides and sarcophytonin B (67) have been reported. 

Marine organisms, particularly corals, have continued to be a source of novel diterpenoids. Cembrenene (72) and mayol (73) are two new cembranoid diterpenoids from the soft coral Sinularia mayi.129 The cembrene alcohol (74) has been... 

Substances with unusual carbon skeletons have been isolated from soft corals of the family Alcyonacea and the closely related Gorgonacea e.g., the sesquiterpenes A. from Lemnalia africana (C Hj O, Mr 222.37, mp. 58-60°C, [alj, -659.5°) and sinularene from Sinularia mayi (C15H24, Mr 204.36, oil, [a]o -142°). 

Cembranolldes. Name for cembranoids containing a lactone ring, e.g., 3,7,11,15 (17)-cembratetraen-16,2-olide, CjoHjsOz, Mr 300.44, oil, [a]j, -29.0° (CHCI3) isolated from the soft coral Sinularia mayi. 

Beechan CM, Djerassi C, Eggert H (1978) Terpenoids 74. Sesquiterpenes from Soft Coral Sinularia mayi. Tetrahedron 34 2503... 

Source Sinularia mayi Luttschw. Mol. formula C2QH2g02 Mol. wt. 300 Solvent CDC1 ... 

UcHio, Y., H. Nabeya, M. Nakayama, S. Hayashi, and T. Hash Cembrenene and Mayol, Two New Cembranoid Diterpenes from the Soft Coral Sinularia mayi. Tetrahedron Lett. 22, 1689 (1981). 

Scheme 11.31). Indeed, in their synthesis of this attractive sesquiterpene isolated from both marine coral Sinularia mayi and Amazonian tree Xylopia brasiliensis, three different catalytic systems were combined in one pot without decreasing the overall efficiency of the reactions. The catalytic sequence is initiated by cross-metathesis between 2 and 121. Subsequent addition of 120 and (5)-3 in the same vessel allows for the asymmetric Michael addition, and further addition of L-proline induces the final intramolecular Michael addition. The efficiency of the sequence is demonstrated by the high stereoselectivity obtained (5 1 dr, 99% ee) in the construction of this complex skeleton from readily available starting materials. 

Beechan, C.M., Djerassi, C., Finer, J.S., and Clardy, J. (1977) Terpenoids LXXIII. Sinularene, a sesquiterpene hydrocarbon based on a novel skeleton from the soft coral, Sinularia mayi. Tetrahedron Lett., 18, 2395-2398. 

Kobayashi, M. (1994b) Marine terpenes and terpenoids Part 18. First natural 4-tocopherol and A—tocopheryl quinone derivatives with oxygenated side chain, isolated from soft coral Sinularia mayi. J. Chem, Res, (S), 494- 95. 

Nagaoka, H., Iwashima, M., Abe, H., Iguchi, K., and Yamada, Y. (1992) Total synthesis of (+)-mayolide A absolute structure of mayolide A, a secocembrane diterpenoid from the soft coral Sinularia mayi. Chem. Pharm. Bull., 40,1742-1749. 

Collins, P.A. and Wege, D. (1979) The total synthesis of sinularene, a sesquiterpene hydrocarbon from the soft coral Sinularia mayi. Aust. J. Chem., 32, 1819-1826. 

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