Pyrroloquinazolinone Alkaloids 3.1.1

Vasicinone and Related Alkaloids

Application of quinazolinone annelation method (see Sect. 2.1.4) to pyrro-lidinone 71 provides a facile synthesis of deoxyvacisinone 11 [143-145] (Scheme 15). Cyclization of 2-azidobenzoyl derivative 72 via iminophos-phorane 73 to 2,3-dihydropyrrolo[2,1-fr]quinazolin-9(1ff)-one (11) proceeds more rapidly with tributylphosphine (TBP) than with TPP in accordance with the general reactivity trend; however, steric effects should also be considered as an important factor in these aza-Wittig reactions.

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