{'fraction_non_alphanumeric': 0.02541544477028348, 'fraction_numerical': 0.021505376344086023, 'mean_word_length': 4.953488372093023, 'pattern_counts': {'":': 0, '<': 0, '<?xml version=': 0, '>': 0, 'https://': 0, 'lorem ipsum': 0, 'www.': 0, 'xml': 0}, 'pii_count': 0, 'substrings_counts': 0, 'word_list_counts': {'cursed_substrings.json': 0, 'profanity_word_list.json': 0, 'sexual_word_list.json': 0, 'zh_pornsignals.json': 0}}
Studies Directed toward the Synthesis of the Unusual Antileukemic Diterpene Jatrophatrione. 2. Functionalization of Advanced Polycyclic Precursors to the 9-Epi and 8,9-Dehydro Congeners.

The synthesis of highly functionalized [5.9.5]tricyclic systems closely related to jatrophatrione (1) and 9-epijatrophatrione (2) is described. The first set of experiments provides a route to the conjugated 7-methylene ketones 8 and 9, both of which resist migration of the exocyclic double bond to a position internal to the ring. Subsequent dihydroxylation studies define a convenient pathway from 3 to triketone 20, which has yet to exhibit a tendency to undergo appropriate dehydration at the tertiary carbinol center. The presence of a carbonyl group in ring C was shown not to be contributory to this low reactivity. Finally, a protocol involving formation of a bromo oxetane with subsequent introduction of a C8-C9 double bond and Grob fragmentation has shown promise for arrival at 1 and/or 2 by making available the diene 36.