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Volumn 53, Issue 25, 2014, Pages 6419-6424

Spontaneous biomimetic formation of (±)-dictazole B under irradiation with artificial sunlight

Author keywords

alkaloids; aplysinopsin; biomimetic synthesis; natural products; self assembly

Indexed keywords

ALKALOIDS; BIOSYNTHESIS; METABOLITES; NITROGEN COMPOUNDS; SELF ASSEMBLY;

EID: 84902245926     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201403454     Document Type: Article
Times cited : (37)

References (50)
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    • For the first isolation and description of aplysinopsin (1), see:, R. Kazlauskas, P. T. Murphy, R. J. Quinn, R. J. Wells, Tetrahedron Lett. 1977, 18, 61-64. For the isolation of its congeners, see Ref. [1]; for a recent example, see
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    • for a description of cycloaplysinopsin C, see
    • For a description of cycloaplysinopsins A and B, see:a) I. Mancini, G. Guella, H. Zibrowius, F. Pietra, Tetrahedron 2003, 59, 8757-8762; for a description of cycloaplysinopsin C, see
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    • See also Ref. [4c] for sunlight-induced E/Z interconversion.
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    • The sponge S. cerebriformis was collected at the northwest coast of Panama from a depth of 2-3 m (Ref. [5a,b]); stony-coral Tubastraea sp. samples were collected in a reef environment from a depth of 3 m at Comoro Islands (Ref. [3a]), from a depth of ca. 3 m at Capsalon Island, Philippines (Ref. [6a] and [3a]), and from a depth of 12 m depth in the Hanish Islands archipelago, Yemen (Ref. [3b]). The depth was not mentioned in the description of the collection of Tubastraea sp. in the Odomari area, Kagoshima prefecture, Japan (Ref. [3a] and [4b]) and for the sponge Ianthella cf. flabelliformis, which was collected at Lonsdale wall, Port Phillip, Australia (38°17'55''S, 144°37'76''E). For the penetration of light into (tropical) sea water, see for example
    • The sponge S. cerebriformis was collected at the northwest coast of Panama from a depth of 2-3 m (Ref. [5a,b]); stony-coral Tubastraea sp. samples were collected in a reef environment from a depth of 3 m at Comoro Islands (Ref. [3a]), from a depth of ca. 3 m at Capsalon Island, Philippines (Ref. [6a] and [3a]), and from a depth of 12 m depth in the Hanish Islands archipelago, Yemen (Ref. [3b]). The depth was not mentioned in the description of the collection of Tubastraea sp. in the Odomari area, Kagoshima prefecture, Japan (Ref. [3a] and [4b]) and for the sponge Ianthella cf. flabelliformis, which was collected at Lonsdale wall, Port Phillip, Australia (38°17'55''S, 144°37'76''E). For the penetration of light into (tropical) sea water, see for example:, R. P. Dunne, B. E. Brown, Mar. Ecol. Prog. Ser. 1996, 144, 109-118
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    • Indeed, preliminary results (LC/MS traces, see Ref. [5b]) indicated a conversion of dictazole A into dictazoline C under microwave activation in water, following the seminal and beautiful conversion of sceptrin into ageliferin under such conditions; see
    • Indeed, preliminary results (LC/MS traces, see Ref. [5b]) indicated a conversion of dictazole A into dictazoline C under microwave activation in water, following the seminal and beautiful conversion of sceptrin into ageliferin under such conditions; see:, B. H. Northrop, D. P. O'Malley, A. L. Zografos, P. S. Baran, Angew. Chem. 2006, 118, 4232-4236
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    • references therein. In the particular case of pyrrole aminoimidazole alkaloids, Molinski and co-workers recently disclosed a crucial step forward in understanding the biosynthesis of this highly diverse family of natural substances; see
    • Angew. Chem. Int. Ed. 2006, 45, 4126-4130, and references therein. In the particular case of pyrrole aminoimidazole alkaloids, Molinski and co-workers recently disclosed a crucial step forward in understanding the biosynthesis of this highly diverse family of natural substances; see
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    • This paper also features a synthetic approach towards dictazole A (6). The special [2+2] photochemical origin of sceptrin has also been discussed, but attempts to realize this [2+2] dimerization have previously been unsuccessful; see
    • W. R. Gutekunst, P. S. Baran, J. Org. Chem. 2014, 79, 2430-2452. This paper also features a synthetic approach towards dictazole A (6). The special [2+2] photochemical origin of sceptrin has also been discussed, but attempts to realize this [2+2] dimerization have previously been unsuccessful; see
    • (2014) J. Org. Chem. , vol.79 , pp. 2430-2452
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    • For the isolation of formylindoles 8 and 9, see, for example (isolation from a Smenospongia sponge).
    • For the isolation of formylindoles 8 and 9, see, for example (isolation from a Smenospongia sponge):, M. J. McKay, A. R. Carroll, R. J. Quinn, J. N. A. Hooper, J. Nat. Prod. 2002, 65, 595-597.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.