Pinna muricata Pinnatoxins

Chou, T., Haino, T., Kuramoto, M., and Uemura, D., Isolation and structure of pinnatoxin D, a new shellfish poison from the Okinawan bivalve Pinna muricata, Tetrahedron Lett., 37, 4027, 1996. 

Uemura, D., Chou, T, Haino, T, Nagatsu, A., Fukuzawa, S., Zheng, S.Z. and Chen, H., 1995. Pinnatoxin A atoxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata. JAm Chem Soc 117, 1155-1156. 

Chou, T, Kamo, O., and Uemura, D. Relative stereochemistry of pinnatoxin A, a potent shellfish poison from Pinna muricata. Tet. Lett., 37, 4023 026, 1996b. 

Takada, N. et al., Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata. Tetrahedron Lett. 42(20), 3491-3494, 2001. 

Pinnatoxins A and D have been isolated from the Pen Shell, Pinna muricata, from Japan [31-33], Pinnatoxins B and C, which are stereoisomers, were isolated as a 1 1 mixture from the same source... 

Pinnatoxins. Mussel toxins from the genus Pinna Pinna attenuata, P. pectinata). These mussels are precious food in the coastal regions of Japan and China and contain varying amounts of P. Poisonings are common but only rarely lethal. The P. are spirocyclic acetals, e.g., P. A C41H61NO, Mr 711,94, [a]n +2.5° (CH,OH), LD99 (mouse i.p.) 180 pg/kg isolated from Pinna muricata see also PSP. 

Pinnatoxin A (197), isolated from the shellfish Pinna muricata, is an important toxic principle in Pinna shellfish intoxieation outbreaks in China and Japan. Its unique molecular architecture, accompanied by its pronounced biological activity as a Ca " -channel activator, makes pinnatoxin an intriguing synthetic target. A MBH analogous reaction, namely, Ni(ii)/Cr(ii)-mediated coupling between aldehyde 198 and 2-iodoacrylic add derivative 199 to give MBH adduct 200 in 88% yield, was utilized as a key step in the total synthesis of (-)-pinnatoxin A (Scheme 5.37). As part of the synthetic strategy, a biomimetic intramolecular Diels-Alder reaction was developed to construct the macrocyclic structure of (-)-pinnatoxin A. 

Uemura D, Chou T, Haino T, Nagatsu A, Fukuzawa S, Zheng SZ, Chen H (1995) Pinnatoxin A a toxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata. J Am Chem Soc 117 1155... 

A series of macrocyclic compoimds possessing a unique dispiroacetal l,7,9-trioxadispiro[5.1.5.2]pentadecane and a bicyclic acetal 6,8-dioxabi cyclo[ 3.2.1] octane concomitant with a spirocycHc imine part were isolated from marine bivalves. Pinnatoxin A (104) was isolated from the Okinawan bivalve Pinna muricata [50,51] and pinnatoxins B (105) and C (106) [52], and pteriatoxins A-C (107-109) were isolated from Pinna penguin [53]. These compounds seem to be responsible for Pinna shellfish poisonings in China and Japan, as Ca " activators [54]. In addition, analogous compounds without the bicyclic acetal, spiroHdes A-E (110-114), were produced by the dinoflagellate Alexandrium ostenfeldii [55,56]. 

Pinnatoxin A 3, isolated from the shellfish Pinna muricata, is thought to be a calcium channel activator. A key transformation in the s mthesis of3 reported J. Am. Chem. Soc. 2008,130, 3774) by Armen Zakarian, now at the University of California, Santa Barbara, was the diaste-reoselective Claisen rearrangement of 1 to 2. 

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