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1 article(s) from Kumamoto, Takuya

Diels- Alder reactions using 4,7-dioxygenated indanones as dienophiles for regioselective construction of oxygenated 2,3-dihydrobenz[f]indenone skeleton

Natsuno Etomi,
Takuya Kumamoto,
Waka Nakanishi and
Tsutomu Ishikawa

Beilstein J. Org. Chem. 2008, 4, No. 15, doi:10.3762/bjoc.4.15

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Graphical Abstract

Figure 1: The structure of kinamycins.

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Scheme 1: Retrosynthesis of kinamycins.

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Scheme 2: Synthesis of quinones 8 and 12 and the acetals 13 and 14. Reagents and conditions: a) P₂O₅, CH₃SO₃H...

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Figure 2: Selected HMBC correlations (lines) and NOE enhancements (dash) on 21 (a) and on 22 (b).

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Scheme 3: DAR of benzyne 10 and furan (9). Reagents and conditions: a) ethylene glycol, PPTS, benzene, reflux...

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Figure 3: Selected HMBC correlations (a) and NOE enhancements (b) on the ring-opened product 27.

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Figure 4: Transition states supposed for the regioselective DAR via quinone route.

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Figure 5: Representative LUMO coeffients of quinones 8 and 12 (a) and their reaction courses with diene 7 (b)....

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Scheme 4: The proposed mechanism for the acid-induced ring opening of epoxynaphthalene 29 by Giles et al. [19].

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Scheme 5: Supposed reaction pathways for the acid-induced ring opening of 11.

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Published 15 May 2008

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