Short and flexible route to 3,4-diarylpyrrole marine alkaloids: syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether

Iwao, Masatomo; Takeuchi, Toshiro; Fujikawa, Naotaka; Fukuda, Tsutomu; Ishibashi, Fumito

doi:10.1016/s0040-4039(03)01031-1

Cited by 86 publications

(41 citation statements)

References 46 publications

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“…6 Thus, in the present synthesis, we planned to synthesize the pinacol coupling precursor 7 via a palladium-catalyzed cross-coupling reaction of triflate 10 with indole-3-boronate 11 having an aldehyde equivalent substituent at the 2-position. The intermediate triflate 10 has been prepared as an intermediate in our previous synthesis of 3,4-diarylpyrrole marine alkaloids 7 by a Suzuki-Miyaura cross-coupling reaction of 3,4-dihydroxypyrrole bistriflate 12 obtained via a Hinsberg-type reaction of iminodiacetate 13.…”

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confidence: 99%

A formal total synthesis of the telomerase inhibitor dictyodendrin B

Hirao

Yoshinaga

Iwao

et al. 2010

Tetrahedron Letters

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confidence: 99%

A formal total synthesis of the telomerase inhibitor dictyodendrin B

Hirao

Yoshinaga

Iwao

et al. 2010

Tetrahedron Letters

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“…1). The storniamide marine alkaloids were first isolated in 1996 by Seldes and coworkers 17 and subsequently Takamura 18 (2009), Iwao 19 (2003), Furstner 2 (2002), Boger 20 (1999), Steglich 21 (1998) and our group 22 (2008) reported either total or formal syntheses of permethyl storniamide A (7, Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether

et al. 2014

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Lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether are pyrrole containing, natural products, which exhibit interesting biological properties. Such properties include anti-tumor activity on a variety of cancer cell lines including those that confer drug resistance, inhibition of HIV integrase and vascular disrupting activity. We now describe the use of methyl and ethyl 3-bromo-2-formylpyrrole-5-carboxylate as building blocks for the formal synthesis of these three highly functionalized, bioactive pyrroles. These new building blocks will now provide ready access to the natural products and many novel analogs due to the ability to easily modify positions 2,3,4 and 5 of the pyrrole core.

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“…[56][57][58] For example, the total synthesis of lamellarins L (26) and N (105) is shown in Scheme 16. Intermediate (110) was prepared by convergent assembly of bistriflate (106) and arylboronic acids (107) and (108) in a similar manner as described above.…”

Section: -2-2 Synthesis By Iwao (I)mentioning

confidence: 99%